(6-allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-trimethyl-silane

Base Information

• Chemical Name: (6-allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-trimethyl-silane
• CAS No.: 931098-45-2
• Molecular Formula: C₂₇H₃₈O₆Si
• Molecular Weight: 486.681
• Mol file: 931098-45-2.mol

Synonyms:(6-allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-trimethyl-silane

Chemical Property of (6-allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-trimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6-allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-trimethyl-silane

There total 7 articles about (6-allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-trimethyl-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: 98.0%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + allyl 2,6-dibenzyl-3-methyl-α-D-mannopyranoside (187732-08-7) → (6-allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-trimethyl-silane (931098-45-2)

Guidance literature:

With triethylamine; In dichloromethane; for 0.5h;

DOI:10.1021/jo061991n

Reference yield:

1-O-allyl-3-O-methyl-4,6-benzylidene-D-mannose → (6-allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-trimethyl-silane (931098-45-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 66 percent / NaH; imidazole / tetrahydrofuran; dimethylformamide / 1 h

2: 73 percent / NaBH₃CN; TiCl₄ / acetonitrile / 3 h / 0 °C

3: 98 percent / Et₃N / CH₂Cl₂ / 0.5 h

With 1H-imidazole; titanium tetrachloride; sodium hydride; sodium cyanoborohydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo061991n

Reference yield:

6-allyloxy-7-benzyloxy-8-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (194594-69-9) → (6-allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-trimethyl-silane (931098-45-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / NaBH₃CN; TiCl₄ / acetonitrile / 3 h / 0 °C

2: 98 percent / Et₃N / CH₂Cl₂ / 0.5 h

With titanium tetrachloride; sodium cyanoborohydride; triethylamine; In dichloromethane; acetonitrile;

DOI:10.1021/jo061991n

upstream raw materials:

trimethylsilyl trifluoromethanesulfonate

allyl 2,6-dibenzyl-3-methyl-α-D-mannopyranoside

6-allyloxy-7-benzyloxy-8-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

D-Mannose

Downstream raw materials:

benzoic acid 6-(6-allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yl ester

(2R,3R,4S,5S,6R)-6-((2R,3R,4S,5S,6S)-6-Allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-ol

allyl 2,6-dibenzyl-3-methyl-α-D-mannopyranoside

[6-(6-allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy]-trimethyl-silane