1,2,3,4-Tetra-O-acetyl-β-D-glucuronic acid methyl ester

Basic information

  • Product Name:1,2,3,4-Tetra-O-acetyl-β-D-glucuronic acid methyl ester
  • CasNo.:7355-18-2
  • MF:C15H20 O11
  • MW:376.317

Physical and Chemical Properties

  • Boiling Point:179 °C
  • Packing:
  • Throughput:
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Product Details

CasNo: 7355-18-2

MF: C15H20 O11

Appearance: White Powder

Manufacturers supply cost-effective and customizable 1,2,3,4-Tetra-O-acetyl-β-D-glucuronic acid methyl ester 7355-18-2

Synonyms: Methyl 1,2,3,4-tetra-acetyl-D-glucopyranuronate;Methyl 1,2,3,4-Tetra-O-acetyl β-D-glucuronate;

Molecular Formula:  C15H20O11

Molecular Weight: 376.31 

CAS Number7355-18-2

Molecular Structure:

 Specification:       

Item

Specification

Appearance

White to off-white powder

Assay (GC),%

≥98.0

Specific rotation [α]20(C=1,CHCl3

 +6.0~+11.0°

Loss on drying,%

≤0.5

Residue on ignition,%

≤0.5

METHYL 1,2,3,4-TETRA-O-ACETYL-BETA-D-GLUCURONATE(Cas 7355-18-2) Usage

Glycoside pharmaceutical intermediates.

7355-18-2 Relevant articles

Synthesis of a Macrocyclic Conjugate of the Diterpenoid Isosteviol and Glucuronic Acid

Andreeva,Sharipova,Garifullin,Strobykina, I. Yu.,Kataev

, p. 689 - 692 (2015)

A macrocyclic conjugate of the natural d...

Synthesis and antitubercular activity of first glucuronosyl phosphates and amidophosphates containing polymethylene chains

Izmest’ev,Andreeva,Sharipova,Kravchenko,Garifullin,Strobykina, I. Yu.,Kataev,Mironov

, p. 51 - 56 (2017)

Novel phosphorylated glycolipids based o...

Bile alcohol glucuronides: Regioselective O-glucuronidation of 5β-cholestane-3α,7α,12α,25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-tetrol

Dayal,Salen,Padia,Shefer,Tint,Sasso,Williams

, p. 133 - 142 (1993)

A facile and regiocontrolled procedure f...

Solid state structure of sodium β-1-thiophenyl glucuronate identifies 5-coordinate sodium with three independent glucoronates

Alharthi, Fahad Ayesh,Whitehead, George F.S.,Vitórica-Yrezábal, I?igo J.,Gardiner, John M.

, (2021/03/29)

Glucuronic acid is a key component of th...

Design, synthesis and biological evaluation of carbohydrate-based sulphonamide derivatives as topical antiglaucoma agents through selective inhibition of carbonic anhydrase II

Fan, Zhanfang,Guo, Chun,Hou, Zhuang,Li, Chuanchao,Lin, Bin,Liu, Yang,Liu, Yichuang,Wang, Yitong,Zhang, Miao

, p. 383 - 390 (2019/12/30)

A series of new carbohydrate-based sulph...

Potent and Prolonged Innate Immune Activation by Enzyme-Responsive Imidazoquinoline TLR7/8 Agonist Prodrug Vesicles

Wang, Bi,Van Herck, Simon,Chen, Yong,Bai, Xiangyang,Zhong, Zifu,Deswarte, Kim,Lambrecht, Bart N.,Sanders, Niek N.,Lienenklaus, Stefan,Scheeren, Hans W.,David, Sunil A.,Kiessling, Fabian,Lammers, Twan,De Geest, Bruno G.,Shi, Yang

supporting information, p. 12133 - 12139 (2020/08/06)

Synthetic immune-stimulatory drugs such ...

Efficient Synthesis of Muramic and Glucuronic Acid Glycodendrimers as Dengue Virus Antagonists

García-Oliva, Cecilia,Cabanillas, Alfredo H.,Perona, Almudena,Hoyos, Pilar,Rumbero, ángel,Hernáiz, María J.

supporting information, p. 1588 - 1596 (2020/02/05)

Carbohydrates are involved in many impor...

7355-18-2 Process route

acetic anhydride
108-24-7

acetic anhydride

(+)-D-glucuronic acid γ-lactone

(+)-D-glucuronic acid γ-lactone

(2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester
7355-18-2

(2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Conditions
Conditions Yield
(+)-D-glucuronic acid γ-lactone; With sodium hydroxide; In methanol; at 0 - 28 ℃; for 2h;
acetic anhydride; With triethylamine; for 0.416667h; Time; Reagent/catalyst; Temperature;
84.31%
methanol
67-56-1

methanol

D-glucurono-6,3-lactone
63-29-6,487-44-5,575-64-4,14362-29-9,18281-92-0,26623-21-2

D-glucurono-6,3-lactone

acetic anhydride
108-24-7

acetic anhydride

(2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester
7355-18-2

(2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Conditions
Conditions Yield
methanol; D-glucurono-6,3-lactone; With sodium hydroxide; at 20 ℃; for 2h;
acetic anhydride; With pyridine; at 0 - 20 ℃; for 3h;
65%
methanol; D-glucurono-6,3-lactone; With sodium hydroxide; at 20 ℃; for 1h;
acetic anhydride; With pyridine; at 4 ℃; for 14h;
57%
methanol; D-glucurono-6,3-lactone; With N,N-dimethyl-ethanamine; for 16h;
acetic anhydride; With sodium acetate; for 96h;
39%
methanol; D-glucurono-6,3-lactone; With N,N-dimethyl-ethanamine; for 3h;
acetic anhydride; With sodium acetate; for 192h;
35%

7355-18-2 Upstream products

  • 110-86-1
    110-86-1

    pyridine

  • 52613-19-1
    52613-19-1

    glucuronic acid methyl ester

  • 108-24-7
    108-24-7

    acetic anhydride

  • 127-09-3
    127-09-3

    sodium acetate

7355-18-2 Downstream products

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    92420-85-4

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    O2,O3,O4-triacetyl-O1-(4-bromo-phenyl)-β-D-glucopyranuronic acid methyl ester

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    O2,O3,O4-triacetyl-O1-[1]naphthyl-β-D-glucopyranuronic acid methyl ester

  • 4630-61-9
    4630-61-9

    2,3,4-tri-O-acetyl-1-O-phenyl-β-D-glucopyranuronic acid methyl ester