L-Idopyranuronic acid, 3-O-(phenylmethyl)-, methyl ester, triacetate

Base Information

• Chemical Name: L-Idopyranuronic acid, 3-O-(phenylmethyl)-, methyl ester, triacetate
• CAS No.: 93382-47-9
• Molecular Formula: C20H24 O10
• Molecular Weight: 424.405
• Mol file: 93382-47-9.mol

Synonyms:L-Idopyranuronic acid, 3-O-(phenylmethyl)-, methyl ester, triacetate

Chemical Property of L-Idopyranuronic acid, 3-O-(phenylmethyl)-, methyl ester, triacetate

Chemical Property:

• Boiling Point: 493.9±45.0 °C (760 mmHg)
• PSA: 123.66000
• Density: 1.29±0.1 g/cm3 (20 °C, 760 mmHg)
• LogP: 0.89620

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-Idopyranuronic acid, 3-O-(phenylmethyl)-, methyl ester, triacetate

There total 28 articles about L-Idopyranuronic acid, 3-O-(phenylmethyl)-, methyl ester, triacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

methyl 3-O-benzyl-β-L-idopyranuronate (87326-78-1) + acetyl chloride (75-36-5) → methyl (acetyl 2,4-di-O-acetyl-3-O-benzyl-α,β-L-idopyranoside)uronate (93382-47-9)

Guidance literature:

With pyridine; 2,4-dimethylaminopyridine; In dichloromethane; at -40 ℃; for 10h;

DOI:10.1002/ejoc.200300254

Reference yield: 71.0%

acetic anhydride (108-24-7) + methyl 1,2-di-O-acetyl-3-O-benzyl-L-idopyranosyluronate → methyl (acetyl 2,4-di-O-acetyl-3-O-benzyl-α,β-L-idopyranoside)uronate (93382-47-9)

Guidance literature:

In pyridine; at 20 ℃;

DOI:10.1016/j.carres.2004.03.006

Reference yield:

methyl 3-O-benzyl-L-idopyranosyluronate (87326-77-0,87326-78-1) + acetyl chloride (75-36-5) → methyl (acetyl 2,4-di-O-acetyl-3-O-benzyl-α,β-L-idopyranoside)uronate (93382-47-9)

Guidance literature:

With pyridine; at 0 - 20 ℃; Industry scale;

upstream raw materials:

acetic anhydride

methyl 3-O-benzyl-1,2-O-isopropylidene-α-L-idofuranosiduronate

diazomethane

(2R,3S,4S,5R)-3,5,6-Triacetoxy-4-benzyloxy-tetrahydro-pyran-2-carboxylic acid

Downstream raw materials:

methyl (2,4-di-O-acetyl-3-O-benzyl-α-L-idopyranosyl bromide)uronate

methyl 3-O-benzyl-4-O-monochloroacetyl-β-L-idopyranuronate 1,2-(tert-butyl orthoacetate)

methyl (phenyl 2,4-di-O-acetyl-3-O-benzyl-1-thio-α-L-idopyranoside)uronate

allyl (methyl 3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside

Refernces

• 1、 Kuszmann, Janos,Medgyes, Gabor,Boros, Sandor. "Synthesis of 2,5-anhydro-(β-D-glucopyranosyluronate)- and (α-L-idopyranosyluronate)-D-mannitol hexa-O-sulfonate hepta sodium salt". . p. 1569 - 1579. Retrieved 2007/10/03.
• 2、 Gavard, Ollivier,Hersant, Yael,Alais, Jocelyne,Duverger, Veronique,Dilhas, Anna,Bascou, Alison,Bonnaffe, David. "Efficient preparation of three building blocks for the synthesis of heparan sulfate fragments: Towards the combinatorial synthesis of oligosaccharides from hypervariable regions". . p. 3603 - 3620. Retrieved 2007/10/03.