(3S,4R,5S)-3-Azido-4-(dimethyl-phenyl-silanyl)-5-((R)-1-hydroxy-ethyl)-tetrahydro-furan-2-ol

Base Information

• Chemical Name: (3S,4R,5S)-3-Azido-4-(dimethyl-phenyl-silanyl)-5-((R)-1-hydroxy-ethyl)-tetrahydro-furan-2-ol
• CAS No.: 1026943-12-3
• Molecular Formula: C₁₄H₂₁N₃O₃Si
• Molecular Weight: 307.425

Synonyms:(3S,4R,5S)-3-Azido-4-(dimethyl-phenyl-silanyl)-5-((R)-1-hydroxy-ethyl)-tetrahydro-furan-2-ol

Chemical Property of (3S,4R,5S)-3-Azido-4-(dimethyl-phenyl-silanyl)-5-((R)-1-hydroxy-ethyl)-tetrahydro-furan-2-ol

Chemical Property:

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Technology Process of (3S,4R,5S)-3-Azido-4-(dimethyl-phenyl-silanyl)-5-((R)-1-hydroxy-ethyl)-tetrahydro-furan-2-ol

There total 2 articles about (3S,4R,5S)-3-Azido-4-(dimethyl-phenyl-silanyl)-5-((R)-1-hydroxy-ethyl)-tetrahydro-furan-2-ol 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:

(3S,4R,5S)-3-Azido-4-(dimethyl-phenyl-silanyl)-5-((R)-1-hydroxy-ethyl)-dihydro-furan-2-one (146328-53-2) → (3S,4R,5S)-3-Azido-4-(dimethyl-phenyl-silanyl)-5-((R)-1-hydroxy-ethyl)-tetrahydro-furan-2-ol (1026943-12-3)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃;

DOI:10.1021/jo00054a002

Reference yield:

(E)-(2S,3S)-2-Azido-3-(dimethyl-phenyl-silanyl)-hex-4-enoic acid methyl ester (136824-24-3) → (3S,4R,5S)-3-Azido-4-(dimethyl-phenyl-silanyl)-5-((R)-1-hydroxy-ethyl)-tetrahydro-furan-2-ol (1026943-12-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) OsO₄, Me₃NO, 2) 5percent aq. HCl / 1) acetone, water, 0 deg C to r.t.

2: DIBAL / CH₂Cl₂ / -78 °C

With hydrogenchloride; osmium(VIII) oxide; trimethylamine-N-oxide; diisobutylaluminium hydride; In dichloromethane;

DOI:10.1021/jo00054a002

Reference yield:

methanol (67-56-1) + (3S,4R,5S)-3-Azido-4-(dimethyl-phenyl-silanyl)-5-((R)-1-hydroxy-ethyl)-tetrahydro-furan-2-ol (1026943-12-3) → (R)-1-[(2S,3R,4S)-4-Azido-3-(dimethyl-phenyl-silanyl)-5-methoxy-tetrahydro-furan-2-yl]-ethanol

Guidance literature:

With acetyl chloride; Yield given; Ambient temperature;

DOI:10.1021/jo00054a002

upstream raw materials:

(3S,4R,5S)-3-Azido-4-(dimethyl-phenyl-silanyl)-5-((R)-1-hydroxy-ethyl)-dihydro-furan-2-one

(E)-(2S,3S)-2-Azido-3-(dimethyl-phenyl-silanyl)-hex-4-enoic acid methyl ester

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