methyl 2,3-di-O-benzyl-α-D-gluco-hexadiolo-1,5-pyranoside

Base Information

• Chemical Name: methyl 2,3-di-O-benzyl-α-D-gluco-hexadiolo-1,5-pyranoside
• CAS No.: 89731-21-5
• Molecular Formula: C₂₁H₂₄O₆
• Molecular Weight: 372.418
• Mol file: 89731-21-5.mol

Synonyms:methyl 2,3-di-O-benzyl-α-D-gluco-hexadiolo-1,5-pyranoside

Chemical Property of methyl 2,3-di-O-benzyl-α-D-gluco-hexadiolo-1,5-pyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3-di-O-benzyl-α-D-gluco-hexadiolo-1,5-pyranoside

There total 1 articles about methyl 2,3-di-O-benzyl-α-D-gluco-hexadiolo-1,5-pyranoside 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: 82.0%

methyl 2,3-di-O-benzyl-α-D-glucopyranoside (17791-36-5) → methyl 2,3-di-O-benzyl-α-D-gluco-hexadiolo-1,5-pyranoside (89731-21-5)

Guidance literature:

With N-chloro-succinimide; methyl-phenyl-thioether; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -10 ℃;

DOI:10.1016/S0040-4039(00)94210-2

Reference yield: 82.0%

methyl 2,3-di-O-benzyl-α-D-gluco-hexadiolo-1,5-pyranoside (89731-21-5) + 1,3-dioxolan-2-ylmethylenetriphenylphosphorane (78950-65-9) → methyl 2,3-di-O-benzyl-α-D-glucooct-6(Z/E)-enodialdo-1,5-pyranoside ethylene acetal (89731-22-6,89747-98-8)

Guidance literature:

In tetrahydrofuran; dimethyl sulfoxide; at 23 ℃;

DOI:10.1016/S0040-4039(00)94210-2

Reference yield:

methyl 2,3-di-O-benzyl-α-D-gluco-hexadiolo-1,5-pyranoside (89731-21-5) → dimethyl (8R)-6,7-anhydro-2,3-di-O-benzyl-α-D-glucooctadialdo-1,5:8,4-dipyranoside (89731-25-9,89824-76-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / dimethylsulfoxide; tetrahydrofuran / 23 °C

2: 90 percent / pyridinium p-toluenesulfonate / 8 h / Heating

3: 1) N-bromosuccinimide; 2) NaH / 1) DME/water (3:1); 2) DMF, 0 degC

With N-Bromosuccinimide; pyridinium p-toluenesulfonate; sodium hydride; In tetrahydrofuran; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)94210-2

upstream raw materials:

methyl 2,3-di-O-benzyl-α-D-glucopyranoside

Downstream raw materials:

methyl 2,3-di-O-benzyl-α-D-glucooct-6(Z/E)-enodialdo-1,5-pyranoside ethylene acetal

dimethyl(8R)-2,3-di-O-benzyl-6,7-dideoxy-α-D-gluco-octodiald-6-eno-1,5:8,4-dipyranoside

dimethyl (8R)-6,7-anhydro-2,3-di-O-benzyl-α-D-glucooctadialdo-1,5:8,4-dipyranoside

dimethyl (8R)-6,7-anhydro-2,3-di-O-benzyl-β-L-erythro-D-glucooctadialdo-1,5:8,4-dipyranoside