methyl-2,6,7-tridesoxy-2,4-di-C-methyl-3,4-di-O-benzyl-α-D-glucohept-6-enopyranoside

Base Information

• Chemical Name: methyl-2,6,7-tridesoxy-2,4-di-C-methyl-3,4-di-O-benzyl-α-D-glucohept-6-enopyranoside
• CAS No.: 85271-59-6
• Molecular Formula: C₂₄H₃₀O₄
• Molecular Weight: 382.5
• Mol file: 85271-59-6.mol

Synonyms:methyl-2,6,7-tridesoxy-2,4-di-C-methyl-3,4-di-O-benzyl-α-D-glucohept-6-enopyranoside

Chemical Property of methyl-2,6,7-tridesoxy-2,4-di-C-methyl-3,4-di-O-benzyl-α-D-glucohept-6-enopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl-2,6,7-tridesoxy-2,4-di-C-methyl-3,4-di-O-benzyl-α-D-glucohept-6-enopyranoside

There total 22 articles about methyl-2,6,7-tridesoxy-2,4-di-C-methyl-3,4-di-O-benzyl-α-D-glucohept-6-enopyranoside 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: 90.0%

Methyltriphenylphosphonium bromide (1779-49-3) + methyl-2-desoxy-2,4-di-C-methyl-3,4-di-O-benzyl-6-aldo-α-D-glucopyranoside (81076-85-9) → methyl-2,6,7-tridesoxy-2,4-di-C-methyl-3,4-di-O-benzyl-α-D-glucohept-6-enopyranoside (85271-59-6)

Guidance literature:

With n-butyllithium; In hexane; benzene; 1.) 15 min, 2.) reflux, 20 min;

DOI:10.1007/BF01142802

Reference yield: 80.0%

methyl-2-desoxy-2,4-di-C-methyl-3,4-di-O-benzyl-6-aldo-α-D-glucopyranoside (81076-85-9) + Methylenetriphenylphosphorane (19493-09-5) → methyl-2,6,7-tridesoxy-2,4-di-C-methyl-3,4-di-O-benzyl-α-D-glucohept-6-enopyranoside (85271-59-6)

Guidance literature:

In benzene; Heating;

DOI:10.1016/S0040-4039(01)90023-1

Reference yield:

1,6-anhydro-3-O-benzyl-2-desoxy-2,4-di-C-methyl-β-D-glucopyranose (81099-75-4) → methyl-2,6,7-tridesoxy-2,4-di-C-methyl-3,4-di-O-benzyl-α-D-glucohept-6-enopyranoside (85271-59-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / NaH / dimethylformamide / 1.5 h

2: 59 percent / HCl / 2 h / 20 °C

3: 83 percent / DMSO, (COCl)2 / CH₂Cl₂ / 0.42 h / -60 °C

4: 90 percent / n-BuLi / hexane; benzene / 1.) 15 min, 2.) reflux, 20 min

With hydrogenchloride; n-butyllithium; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; In hexane; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1007/BF01142802

upstream raw materials:

Methyltriphenylphosphonium bromide

methyl-2-desoxy-2,4-di-C-methyl-3,4-di-O-benzyl-6-aldo-α-D-glucopyranoside

Methylenetriphenylphosphorane

4-O-allyl-1,6-anhydro-2-deoxy-2-C-methyl-β-D-glucopyranose

Downstream raw materials:

methyl-2,6,7-tridesoxy-2,4-di-C-methyl-3,4-di-O-benzyl-α-D-glucoheptapyranoside