((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-vinyl-tetrahydro-pyran-3-yloxy)-((2R,3R,4R,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-dimethyl-silane

Base Information

• Chemical Name: ((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-vinyl-tetrahydro-pyran-3-yloxy)-((2R,3R,4R,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-dimethyl-silane
• CAS No.: 485386-73-0
• Molecular Formula: C₅₃H₆₂O₁₀Si
• Molecular Weight: 887.155

Synonyms:((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-vinyl-tetrahydro-pyran-3-yloxy)-((2R,3R,4R,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-dimethyl-silane

Chemical Property of ((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-vinyl-tetrahydro-pyran-3-yloxy)-((2R,3R,4R,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-dimethyl-silane

Chemical Property:

Purity/Quality:

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Technology Process of ((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-vinyl-tetrahydro-pyran-3-yloxy)-((2R,3R,4R,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-dimethyl-silane

There total 5 articles about ((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-vinyl-tetrahydro-pyran-3-yloxy)-((2R,3R,4R,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-dimethyl-silane 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: 35.0%

dimethylsilicon dichloride (75-78-5,30107-43-8) + methyl 2,3-di-O-benzyl-6,7-dideoxy-α-D-gluco-hept-6-enopyranoside (236424-93-4) + (2α,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-vinyltetrahydro-2H-pyran-3-ol (294872-82-5) → ((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-vinyl-tetrahydro-pyran-3-yloxy)-((2R,3R,4R,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-dimethyl-silane (485386-73-0)

Guidance literature:

methyl 2,3-di-O-benzyl-6,7-dideoxy-α-D-gluco-hept-6-enopyranoside; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃;

dimethylsilicon dichloride; at -78 - 20 ℃;

(2α,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-vinyltetrahydro-2H-pyran-3-ol; With 1H-imidazole; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/S0040-4039(02)01617-9

Reference yield:

(2S,3R,4R,5R,6R)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-tetrahydro-pyran (118545-10-1) → ((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-vinyl-tetrahydro-pyran-3-yloxy)-((2R,3R,4R,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-dimethyl-silane (485386-73-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 95 percent / CSA / methanol / 0 °C

2.1: 77 percent / TBAF

3.1: nBuLi / hexane; tetrahydrofuran / -78 °C

3.2: -78 - 20 °C

3.3: 35 percent / imidazole / tetrahydrofuran / 20 °C

With n-butyllithium; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol; hexane; 2.1: Swern oxidation;

DOI:10.1016/S0040-4039(02)01617-9

Reference yield:

[(2R,3R,4R,5R,6S)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-methanol (305815-34-3) → ((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-vinyl-tetrahydro-pyran-3-yloxy)-((2R,3R,4R,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-dimethyl-silane (485386-73-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 77 percent / TBAF

2.1: nBuLi / hexane; tetrahydrofuran / -78 °C

2.2: -78 - 20 °C

2.3: 35 percent / imidazole / tetrahydrofuran / 20 °C

With n-butyllithium; tetrabutyl ammonium fluoride; In tetrahydrofuran; hexane; 1.1: Swern oxidation;

DOI:10.1016/S0040-4039(02)01617-9

upstream raw materials:

dimethylsilicon dichloride

methyl 2,3-di-O-benzyl-6,7-dideoxy-α-D-gluco-hept-6-enopyranoside

(2α,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-vinyltetrahydro-2H-pyran-3-ol

(2S,3R,4R,5R,6R)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-tetrahydro-pyran

Downstream raw materials:

(E)-(1S,2R,3R,4aR,6aR,8S,9R,10R,10aR,13aS)-1,2,9,10-Tetrakis-benzyloxy-3-benzyloxymethyl-8-methoxy-12,12-dimethyl-1,2,3,4a,6a,8,9,10,10a,13a-decahydro-4,7,11,13-tetraoxa-12-sila-dibenzo[a,e]cyclononene

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