((1R,2R,4S,5R,6S)-4-Benzyloxy-2-benzyloxymethyl-1-methyl-3,7-dioxa-bicyclo[4.1.0]hept-5-yloxy)-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: ((1R,2R,4S,5R,6S)-4-Benzyloxy-2-benzyloxymethyl-1-methyl-3,7-dioxa-bicyclo[4.1.0]hept-5-yloxy)-tert-butyl-dimethyl-silane
• CAS No.: 345342-64-5
• Molecular Formula: C₂₇H₃₈O₅Si
• Molecular Weight: 470.681
• Mol file: 345342-64-5.mol

Synonyms:((1R,2R,4S,5R,6S)-4-Benzyloxy-2-benzyloxymethyl-1-methyl-3,7-dioxa-bicyclo[4.1.0]hept-5-yloxy)-tert-butyl-dimethyl-silane

Chemical Property of ((1R,2R,4S,5R,6S)-4-Benzyloxy-2-benzyloxymethyl-1-methyl-3,7-dioxa-bicyclo[4.1.0]hept-5-yloxy)-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((1R,2R,4S,5R,6S)-4-Benzyloxy-2-benzyloxymethyl-1-methyl-3,7-dioxa-bicyclo[4.1.0]hept-5-yloxy)-tert-butyl-dimethyl-silane

There total 9 articles about ((1R,2R,4S,5R,6S)-4-Benzyloxy-2-benzyloxymethyl-1-methyl-3,7-dioxa-bicyclo[4.1.0]hept-5-yloxy)-tert-butyl-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: 90.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (1R,2R,4S,5R,6S)-4-Benzyloxy-2-benzyloxymethyl-1-methyl-3,7-dioxa-bicyclo[4.1.0]heptan-5-ol (345342-57-6) → ((1R,2R,4S,5R,6S)-4-Benzyloxy-2-benzyloxymethyl-1-methyl-3,7-dioxa-bicyclo[4.1.0]hept-5-yloxy)-tert-butyl-dimethyl-silane (345342-64-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)00355-0

Reference yield:

benzyl 4,6-O-(phenylmethylene)-α-D-glucopyranoside (79549-73-8) → ((1R,2R,4S,5R,6S)-4-Benzyloxy-2-benzyloxymethyl-1-methyl-3,7-dioxa-bicyclo[4.1.0]hept-5-yloxy)-tert-butyl-dimethyl-silane (345342-64-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 100 percent / NaH / dimethylformamide

2.1: 86 percent / NaBH₃CN; HCl / diethyl ether; tetrahydrofuran

3.1: 98 percent / Dess-Martin periodinane / CH₂Cl₂

4.1: 66 percent / diethyl ether

5.1: 100 percent / p-TsOH / Pd/C / methanol; H₂O

6.1: Bu₂SnO / benzene

6.2: 91 percent / Et₃N / dioxane

7.1: 94 percent / i-Pr₂NEt / CH₂Cl₂

8.1: 95 percent / NaH / tetrahydrofuran; methanol

9.1: 90 percent / imidazole / dimethylformamide

With 1H-imidazole; hydrogenchloride; sodium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; benzene; 3.1: Dess-Martin oxidation;

DOI:10.1016/S0040-4039(01)00355-0

Reference yield:

(2R,4R,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-dihydro-pyran-3-one (345342-55-4) → ((1R,2R,4S,5R,6S)-4-Benzyloxy-2-benzyloxymethyl-1-methyl-3,7-dioxa-bicyclo[4.1.0]hept-5-yloxy)-tert-butyl-dimethyl-silane (345342-64-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 66 percent / diethyl ether

2.1: 100 percent / p-TsOH / Pd/C / methanol; H₂O

3.1: Bu₂SnO / benzene

3.2: 91 percent / Et₃N / dioxane

4.1: 94 percent / i-Pr₂NEt / CH₂Cl₂

5.1: 95 percent / NaH / tetrahydrofuran; methanol

6.1: 90 percent / imidazole / dimethylformamide

With 1H-imidazole; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(01)00355-0

upstream raw materials:

tert-butyldimethylsilyl chloride

(1R,2R,4S,5R,6S)-4-Benzyloxy-2-benzyloxymethyl-1-methyl-3,7-dioxa-bicyclo[4.1.0]heptan-5-ol

benzyl 4,6-O-(phenylmethylene)-α-D-glucopyranoside

(2R,3S,4R,5R,6S)-6-Benzyloxy-2-benzyloxymethyl-3-methyl-tetrahydro-pyran-3,4,5-triol