(5S,6R)-3-hydroxymethyl-5-O-tert-butyl-diphenylsilyl-6,7-O-cyclohexylidene-5,6,7-trihydroxy-hept-1-ene

Base Information

Chemical Name:(5S,6R)-3-hydroxymethyl-5-O-tert-butyl-diphenylsilyl-6,7-O-cyclohexylidene-5,6,7-trihydroxy-hept-1-ene
CAS No.:1312413-13-0
Molecular Formula:C₃₀H₄₂O₄Si
Molecular Weight:494.747
Hs Code.:

Synonyms:(5S,6R)-3-hydroxymethyl-5-O-tert-butyl-diphenylsilyl-6,7-O-cyclohexylidene-5,6,7-trihydroxy-hept-1-ene

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Chemical Property of (5S,6R)-3-hydroxymethyl-5-O-tert-butyl-diphenylsilyl-6,7-O-cyclohexylidene-5,6,7-trihydroxy-hept-1-ene

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Technology Process of (5S,6R)-3-hydroxymethyl-5-O-tert-butyl-diphenylsilyl-6,7-O-cyclohexylidene-5,6,7-trihydroxy-hept-1-ene

There total 6 articles about (5S,6R)-3-hydroxymethyl-5-O-tert-butyl-diphenylsilyl-6,7-O-cyclohexylidene-5,6,7-trihydroxy-hept-1-ene 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: 70.0%

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 1312413-11-8
(5S,6R)-1-bromo-5-O-tert-butyl-diphenylsilyl-6,7-O-cyclohexylidene-5,6,7-trihydroxy-hept-2E-ene

: 1312413-13-0
(5S,6R)-3-hydroxymethyl-5-O-tert-butyl-diphenylsilyl-6,7-O-cyclohexylidene-5,6,7-trihydroxy-hept-1-ene

Guidance literature:: (5S,6R)-1-bromo-5-O-tert-butyl-diphenylsilyl-6,7-O-cyclohexylidene-5,6,7-trihydroxy-hept-2E-ene; With zinc; In tetrahydrofuran; at 25 ℃; for 0.166667h;

formaldehyd; In tetrahydrofuran; at 25 ℃; for 0.5h;

With ammonium chloride; In tetrahydrofuran; water; at 25 ℃;
DOI:10.1021/jo200670v

Reference yield:

: 1197010-57-3
(2R,3S)-3-tert-butyldiphenylsilyloxy-1,2-(cyclohexylidenedioxy)hex-5-ene

: 1312413-13-0
(5S,6R)-3-hydroxymethyl-5-O-tert-butyl-diphenylsilyl-6,7-O-cyclohexylidene-5,6,7-trihydroxy-hept-1-ene

Guidance literature:: Multi-step reaction with 6 steps

1.1: ozone / dichloromethane / 0.25 h / -78 °C

1.2: -78 - 20 °C

2.1: sodium hydride / tetrahydrofuran / 0 - 25 °C / Inert atmosphere

2.2: 0 - 25 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 2 h / -78 °C

4.1: triethylamine / dichloromethane / 0 - 20 °C

5.1: sodium hydrogencarbonate; sodium bromide / acetone / 25 °C

6.1: zinc / tetrahydrofuran / 0.17 h / 25 °C

6.2: 0.5 h / 25 °C

6.3: 25 °C

With sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; ozone; triethylamine; sodium bromide; zinc; In tetrahydrofuran; hexane; dichloromethane; acetone; 2.1: Wittig-Horner olefination / 2.2: Wittig-Horner olefination;
DOI:10.1021/jo200670v

Reference yield:

: 1197010-63-1
(3S,4R)-3-O-tert-butyl-diphenylsilyl-4,5-O-cyclohexylidene-3,4,5-trihydroxy-pentanal

: 1312413-13-0
(5S,6R)-3-hydroxymethyl-5-O-tert-butyl-diphenylsilyl-6,7-O-cyclohexylidene-5,6,7-trihydroxy-hept-1-ene

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydride / tetrahydrofuran / 0 - 25 °C / Inert atmosphere

1.2: 0 - 25 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 2 h / -78 °C

3.1: triethylamine / dichloromethane / 0 - 20 °C

4.1: sodium hydrogencarbonate; sodium bromide / acetone / 25 °C

5.1: zinc / tetrahydrofuran / 0.17 h / 25 °C

5.2: 0.5 h / 25 °C

5.3: 25 °C

With sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; sodium bromide; zinc; In tetrahydrofuran; hexane; dichloromethane; acetone; 1.1: Wittig-Horner olefination / 1.2: Wittig-Horner olefination;
DOI:10.1021/jo200670v