(3S,4R)-3-O-tert-butyl-diphenylsilyl-4,5-O-cyclohexylidene-3,4,5-trihydroxy-pentanal

Base Information

• Chemical Name: (3S,4R)-3-O-tert-butyl-diphenylsilyl-4,5-O-cyclohexylidene-3,4,5-trihydroxy-pentanal
• CAS No.: 1197010-63-1
• Molecular Formula: C₂₇H₃₆O₄Si
• Molecular Weight: 452.666

Synonyms:(3S,4R)-3-O-tert-butyl-diphenylsilyl-4,5-O-cyclohexylidene-3,4,5-trihydroxy-pentanal

Chemical Property of (3S,4R)-3-O-tert-butyl-diphenylsilyl-4,5-O-cyclohexylidene-3,4,5-trihydroxy-pentanal

Chemical Property:

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Technology Process of (3S,4R)-3-O-tert-butyl-diphenylsilyl-4,5-O-cyclohexylidene-3,4,5-trihydroxy-pentanal

There total 1 articles about (3S,4R)-3-O-tert-butyl-diphenylsilyl-4,5-O-cyclohexylidene-3,4,5-trihydroxy-pentanal 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: 86.0%

(2R,3S)-3-tert-butyldiphenylsilyloxy-1,2-(cyclohexylidenedioxy)hex-5-ene (1197010-57-3) → (3S,4R)-3-O-tert-butyl-diphenylsilyl-4,5-O-cyclohexylidene-3,4,5-trihydroxy-pentanal (1197010-63-1)

Guidance literature:

(2R,3S)-3-tert-butyldiphenylsilyloxy-1,2-(cyclohexylidenedioxy)hex-5-ene; With ozone; In dichloromethane; at -78 ℃; for 0.25h;

With triphenylphosphine; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/jo200670v

Reference yield: 80.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + (3S,4R)-3-O-tert-butyl-diphenylsilyl-4,5-O-cyclohexylidene-3,4,5-trihydroxy-pentanal (1197010-63-1) → (5S,6R)-ethyl-5-O-tert-butyl-diphenylsilyl-6,7-O-cyclohexylidene-5,6,7-trihydroxy-hept-2E-enoate (1312413-09-4)

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In tetrahydrofuran; at 0 - 25 ℃; Inert atmosphere;

(3S,4R)-3-O-tert-butyl-diphenylsilyl-4,5-O-cyclohexylidene-3,4,5-trihydroxy-pentanal; In tetrahydrofuran; at 0 - 25 ℃; Inert atmosphere;

DOI:10.1021/jo200670v

Reference yield:

(3S,4R)-3-O-tert-butyl-diphenylsilyl-4,5-O-cyclohexylidene-3,4,5-trihydroxy-pentanal (1197010-63-1) + allyl bromide (106-95-6) → (2R,3S)-1,2-O-cyclohexylidene-3-O-tert-butyldiphen-ylsilyl-1,2,3,5-tetrahydroxy-oct-7-enes (1197010-74-4)

Guidance literature:

With iron(III) chloride; zinc; In tetrahydrofuran; at 10 ℃; for 1.33333h;

DOI:10.1016/j.tetasy.2009.07.030

upstream raw materials:

(2R,3S)-3-tert-butyldiphenylsilyloxy-1,2-(cyclohexylidenedioxy)hex-5-ene

Downstream raw materials:

(2R,3S)-1,2-O-cyclohexylidene-3-O-tert-butyldiphen-ylsilyl-1,2,3,5-tetrahydroxy-oct-7-enes

(5S,6R)-5-O-tert-butyl-diphenylsilyl-6,7-O-cyclohexylidene-1,5,6,7-tetrahydroxy-hept-2E-ene

C₃₀H₄₂O₆SSi

(5S,6R)-1-bromo-5-O-tert-butyl-diphenylsilyl-6,7-O-cyclohexylidene-5,6,7-trihydroxy-hept-2E-ene

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