methyl 2,3-dideoxy-4,6-O-benzylidene-2-methyl-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2,3-dideoxy-4,6-O-benzylidene-2-methyl-α-D-glucopyranoside
• CAS No.: 90365-11-0
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.321
• Mol file: 90365-11-0.mol

Synonyms:methyl 2,3-dideoxy-4,6-O-benzylidene-2-methyl-α-D-glucopyranoside

Chemical Property of methyl 2,3-dideoxy-4,6-O-benzylidene-2-methyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3-dideoxy-4,6-O-benzylidene-2-methyl-α-D-glucopyranoside

There total 1 articles about methyl 2,3-dideoxy-4,6-O-benzylidene-2-methyl-α-D-glucopyranoside 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: 67.0%

methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methylene-α-D-erythro-hexopyranoside (35905-41-0) → methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methyl-α-D-arabino-hexo pyranoside (93381-10-3) + methyl 2,3-dideoxy-4,6-O-benzylidene-2-methyl-α-D-glucopyranoside (90365-11-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; Yields of byproduct given;

DOI:10.1016/S0040-4039(01)80352-X

Reference yield:

methyl 2,3-dideoxy-4,6-O-benzylidene-2-methyl-α-D-glucopyranoside (90365-11-0) → Benzoic acid (2R,3S,5R,6S)-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester (123444-64-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / hydrogen / Pd(OH)2 / ethanol

2: 84 percent / Ph₃P, DIAD / tetrahydrofuran

With di-isopropyl azodicarboxylate; hydrogen; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; ethanol;

DOI:10.1016/S0040-4039(01)80352-X

Reference yield:

methyl 2,3-dideoxy-4,6-O-benzylidene-2-methyl-α-D-glucopyranoside (90365-11-0) → Benzoic acid (2R,3S,5R,6S)-3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / hydrogen / Pd(OH)2 / ethanol

2: 84 percent / Ph₃P, DIAD / tetrahydrofuran

3: 89 percent / imidazole / DMAP / dimethylformamide / 70 °C

With 1H-imidazole; di-isopropyl azodicarboxylate; hydrogen; triphenylphosphine; dmap; palladium dihydroxide; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)80352-X

upstream raw materials:

methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methylene-α-D-erythro-hexopyranoside

Downstream raw materials:

Benzoic acid (2R,3S,5R,6S)-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester

(2R,3S,5R,6S)-2-((E)-(1S,3S,7S,8S)-8,9-Bis-benzyloxy-7-benzyloxymethyl-1-methoxy-3,5-dimethyl-non-5-enyl)-3,6-dimethoxy-5-methyl-tetrahydro-pyran

(E)-(3S,7S,8S)-8,9-Bis-benzyloxy-7-benzyloxymethyl-1-((2S,3S,5R,6S)-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-yl)-3,5-dimethyl-non-5-en-1-one

(E)-(3S,7S,8S)-8,9-Bis-benzyloxy-7-benzyloxymethyl-1-[(2S,3S,5R,6S)-3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-5-methyl-tetrahydro-pyran-2-yl]-3,5-dimethyl-non-5-en-1-one