Methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-6-C-methyl-α-D-gluco-hept-6-eno-1,5-pyranoside

Base Information

• Chemical Name: Methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-6-C-methyl-α-D-gluco-hept-6-eno-1,5-pyranoside
• CAS No.: 138638-94-5
• Molecular Formula: C₃₀H₃₄O₅
• Molecular Weight: 474.597
• Mol file: 138638-94-5.mol

Synonyms:Methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-6-C-methyl-α-D-gluco-hept-6-eno-1,5-pyranoside

Chemical Property of Methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-6-C-methyl-α-D-gluco-hept-6-eno-1,5-pyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-6-C-methyl-α-D-gluco-hept-6-eno-1,5-pyranoside

There total 4 articles about Methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-6-C-methyl-α-D-gluco-hept-6-eno-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 2,3,4-tri-O-benzyl-6-bis-C-<(trimethylsilyl)methyl>-α-D-glucopyranoside (138638-92-3) → Methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-6-C-methyl-α-D-gluco-hept-6-eno-1,5-pyranoside (138638-94-5) + Methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-6-C-methylene-7-C-trimethylsilyl-α-D-gluco-hepto-1,5-pyranoside (138638-93-4)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane;

DOI:10.1016/0008-6215(91)80009-C

Reference yield:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) → Methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-6-C-methyl-α-D-gluco-hept-6-eno-1,5-pyranoside (138638-94-5)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridinium dichromate / dimethylformamide / 16 h / Ambient temperature

2: diethyl ether

3: 1. Mg, I₂ / 1. ether; 2. ether, a.) 0 deg C, b.) 0 deg C to r.t.

4: 13 percent / p-toluenesulfonic acid monohydrate / CH₂Cl₂

With dipyridinium dichromate; iodine; toluene-4-sulfonic acid; magnesium; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(91)80009-C

Reference yield:

(2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-carboxylic acid (120444-48-6) → Methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-6-C-methyl-α-D-gluco-hept-6-eno-1,5-pyranoside (138638-94-5)

Guidance literature:

Multi-step reaction with 3 steps

1: diethyl ether

2: 1. Mg, I₂ / 1. ether; 2. ether, a.) 0 deg C, b.) 0 deg C to r.t.

3: 13 percent / p-toluenesulfonic acid monohydrate / CH₂Cl₂

With iodine; toluene-4-sulfonic acid; magnesium; In diethyl ether; dichloromethane;

DOI:10.1016/0008-6215(91)80009-C

upstream raw materials:

Methyl 2,3,4-tri-O-benzyl-6-bis-C-<(trimethylsilyl)methyl>-α-D-glucopyranoside

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

(2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-carboxylic acid

methyl (methyl-2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate