[(S)-2-((4R,5R)-5-Azido-2,2-dimethyl-[1,3]dioxan-4-yl)-1-benzenesulfinylmethyl-ethoxy]-tert-butyl-diphenyl-silane

Base Information

• Chemical Name: [(S)-2-((4R,5R)-5-Azido-2,2-dimethyl-[1,3]dioxan-4-yl)-1-benzenesulfinylmethyl-ethoxy]-tert-butyl-diphenyl-silane
• CAS No.: 577749-44-1
• Molecular Formula: C₃₁H₃₉N₃O₄SSi
• Molecular Weight: 577.82

Synonyms:[(S)-2-((4R,5R)-5-Azido-2,2-dimethyl-[1,3]dioxan-4-yl)-1-benzenesulfinylmethyl-ethoxy]-tert-butyl-diphenyl-silane

Chemical Property of [(S)-2-((4R,5R)-5-Azido-2,2-dimethyl-[1,3]dioxan-4-yl)-1-benzenesulfinylmethyl-ethoxy]-tert-butyl-diphenyl-silane

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Technology Process of [(S)-2-((4R,5R)-5-Azido-2,2-dimethyl-[1,3]dioxan-4-yl)-1-benzenesulfinylmethyl-ethoxy]-tert-butyl-diphenyl-silane

There total 2 articles about [(S)-2-((4R,5R)-5-Azido-2,2-dimethyl-[1,3]dioxan-4-yl)-1-benzenesulfinylmethyl-ethoxy]-tert-butyl-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: 75.0%

[(S)-1-Benzenesulfinylmethyl-2-((4R,5S)-5-bromo-2,2-dimethyl-[1,3]dioxan-4-yl)-ethoxy]-tert-butyl-diphenyl-silane (577749-43-0) → [(S)-2-((4R,5R)-5-Azido-2,2-dimethyl-[1,3]dioxan-4-yl)-1-benzenesulfinylmethyl-ethoxy]-tert-butyl-diphenyl-silane (577749-44-1)

Guidance literature:

With sodium azide; In dimethyl sulfoxide; at 80 ℃;

DOI:10.1021/jo026892y

Reference yield:

(2S,3R,5S)-6-Benzenesulfinyl-2-bromo-5-(tert-butyl-diphenyl-silanyloxy)-hexane-1,3-diol (577749-42-9) → [(S)-2-((4R,5R)-5-Azido-2,2-dimethyl-[1,3]dioxan-4-yl)-1-benzenesulfinylmethyl-ethoxy]-tert-butyl-diphenyl-silane (577749-44-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / camphor-10-sulfonic acid / acetone / 20 °C

2: 75 percent / NaN₃ / dimethylsulfoxide / 80 °C

With sodium azide; camphor-10-sulfonic acid; In dimethyl sulfoxide; acetone;

DOI:10.1021/jo026892y

Reference yield:

[(S)-2-((4R,5R)-5-Azido-2,2-dimethyl-[1,3]dioxan-4-yl)-1-benzenesulfinylmethyl-ethoxy]-tert-butyl-diphenyl-silane (577749-44-1) → (S)-3-((4R,5R)-5-Azido-2,2-dimethyl-[1,3]dioxan-4-yl)-2-(tert-butyl-diphenyl-silanyloxy)-propionaldehyde

Guidance literature:

With triethylamine; trifluoroacetic anhydride; In dichloromethane; at 20 ℃;

DOI:10.1021/jo026892y

upstream raw materials:

[(S)-1-Benzenesulfinylmethyl-2-((4R,5S)-5-bromo-2,2-dimethyl-[1,3]dioxan-4-yl)-ethoxy]-tert-butyl-diphenyl-silane

(2S,3R,5S)-6-Benzenesulfinyl-2-bromo-5-(tert-butyl-diphenyl-silanyloxy)-hexane-1,3-diol

Downstream raw materials:

(S)-3-((4R,5R)-5-Azido-2,2-dimethyl-[1,3]dioxan-4-yl)-2-(tert-butyl-diphenyl-silanyloxy)-propan-1-ol

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