methyl 2,6-di-O-benzyl-5-C-methoxy-β-D-gulopyranoside

Base Information

• Chemical Name: methyl 2,6-di-O-benzyl-5-C-methoxy-β-D-gulopyranoside
• CAS No.: 216577-78-5
• Molecular Formula: C₂₂H₂₈O₇
• Molecular Weight: 404.46
• Mol file: 216577-78-5.mol

Synonyms:methyl 2,6-di-O-benzyl-5-C-methoxy-β-D-gulopyranoside

Chemical Property of methyl 2,6-di-O-benzyl-5-C-methoxy-β-D-gulopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,6-di-O-benzyl-5-C-methoxy-β-D-gulopyranoside

There total 5 articles about methyl 2,6-di-O-benzyl-5-C-methoxy-β-D-gulopyranoside 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: 76.0%

methyl 4-O-acetyl-3-O-benzoyl-2,6-di-O-benzyl-5-C-methoxy-β-D-gulopyranoside (216577-86-5) → methyl 2,6-di-O-benzyl-5-C-methoxy-β-D-gulopyranoside (216577-78-5)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 15h;

DOI:10.1080/07328309808001891

Reference yield: 66.0%

methyl 4-O-acetyl-2,6-di-O-benzyl-5-C-methoxy-β-D-xylo-hexopyranosyl-3-ulose (216577-87-6) → methyl 2,6-di-O-benzyl-5-C-methoxy-β-D-galactopyranoside (134039-09-1) + methyl 2,6-di-O-benzyl-5-C-methoxy-β-D-gulopyranoside (216577-78-5)

Guidance literature:

With sodium tetrahydroborate; In methanol;

DOI:10.1080/07328309808001891

Reference yield:

methyl 2,6-di-O-benzyl-5-C-methoxy-β-D-galactopyranoside (134039-09-1) → methyl 2,6-di-O-benzyl-5-C-methoxy-β-D-gulopyranoside (216577-78-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / CH₃C(OC₂H₅)3; p-toluenesulfonic acid; triethylamine / toluene; H₂O

2: 80 percent / pyridine

3: 67 percent / toluene / 68 h / 20 °C

4: 76 percent / MeONa / methanol / 15 h / 20 °C

With sodium methylate; toluene-4-sulfonic acid; Triethyl orthoacetate; triethylamine; In pyridine; methanol; water; toluene; 1: Acetylation / 2: Esterification / 3: Substitution / 4: Hydrolysis;

DOI:10.1080/07328309808001891

upstream raw materials:

methyl 4-O-acetyl-2,6-di-O-benzyl-5-C-methoxy-β-D-xylo-hexopyranosyl-3-ulose

methyl 4-O-acetyl-3-O-benzoyl-2,6-di-O-benzyl-5-C-methoxy-β-D-gulopyranoside

methyl 2,6-di-O-benzyl-5-C-methoxy-β-D-galactopyranoside

methyl 4-O-acetyl-2,6-di-O-benzyl-5-C-methoxy-β-D-galactopyranoside

Downstream raw materials:

2,6-di-O-benzyl-L-lyxo-hexos-5-ulose

1,5-di-O-benzyl-1D-chiro-inositol

2,4-di-O-benzyl-2L-(2,3,4,5,6)-pentahydroxycyclohexanone

(2R,3S,4R,5S,6S)-2,3,4,5,6-pentahydroxycyclohexanone