tert-Butyl-((1R,2S,6R,7R,8R)-4,4-dimethyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.0^2,6]undec-7-yloxy)-diphenyl-silane

Base Information

• Chemical Name: tert-Butyl-((1R,2S,6R,7R,8R)-4,4-dimethyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.0^2,6]undec-7-yloxy)-diphenyl-silane
• CAS No.: 90405-80-4
• Molecular Formula: C₂₅H₃₂O₅Si
• Molecular Weight: 440.612

Synonyms:tert-Butyl-((1R,2S,6R,7R,8R)-4,4-dimethyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.0^2,6]undec-7-yloxy)-diphenyl-silane

Chemical Property of tert-Butyl-((1R,2S,6R,7R,8R)-4,4-dimethyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.0^2,6]undec-7-yloxy)-diphenyl-silane

Chemical Property:

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Technology Process of tert-Butyl-((1R,2S,6R,7R,8R)-4,4-dimethyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.0^2,6]undec-7-yloxy)-diphenyl-silane

There total 3 articles about tert-Butyl-((1R,2S,6R,7R,8R)-4,4-dimethyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.0^2,6]undec-7-yloxy)-diphenyl-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: 92.0%

1,6-anhydro-2,3-O-isopropylidene-β-D-mannopyranose (14440-51-8) + tert-butylchlorodiphenylsilane (58479-61-1) → tert-Butyl-((1R,2S,6R,7R,8R)-4,4-dimethyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.02,6]undec-7-yloxy)-diphenyl-silane (90405-80-4)

Guidance literature:

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

DOI:10.1016/S0040-4039(97)00460-7

Reference yield:

D-Mannose (530-26-7) → tert-Butyl-((1R,2S,6R,7R,8R)-4,4-dimethyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.02,6]undec-7-yloxy)-diphenyl-silane (90405-80-4)

Guidance literature:

Multi-step reaction with 3 steps

1.2: NaOH / H₂O

2.1: p-TsOH; DMP

3.1: 92 percent / imidazole / dimethylformamide

With 1H-imidazole; phthalic acid dimethyl ester; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; 1.1: Tosylation / 1.2: Cyclization / 2.1: Etherification / 3.1: Substitution;

DOI:10.1021/jo000325y

Reference yield:

mannosan (14168-65-1) → tert-Butyl-((1R,2S,6R,7R,8R)-4,4-dimethyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.02,6]undec-7-yloxy)-diphenyl-silane (90405-80-4)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH; DMP

2: 92 percent / imidazole / dimethylformamide

With 1H-imidazole; phthalic acid dimethyl ester; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; 1: Etherification / 2: Substitution;

DOI:10.1021/jo000325y

upstream raw materials:

1,6-anhydro-2,3-O-isopropylidene-β-D-mannopyranose

tert-butylchlorodiphenylsilane

D-Mannose

mannosan

Downstream raw materials:

1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-β-D-arabino-hexopyran-3-ulose

(1R,2S,3R,4S,5R)-2-(tert-Butyl-diphenyl-silanyloxy)-6,8-dioxa-bicyclo[3.2.1]octane-3,4-diol

(3Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-methoxyimine-β-D-arabino-hexopyranose

(Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-methoxyimine-2-O-(prop-2'-inyl)-β-D-arabino-hexopyranose

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