(3R,4S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-4-hydroxycyclohex-1-enecarbaldehyde

Base Information

Chemical Name:(3R,4S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-4-hydroxycyclohex-1-enecarbaldehyde
CAS No.:1101867-41-7
Molecular Formula:C₁₉H₃₈O₄Si₂
Molecular Weight:386.679
Hs Code.:

Synonyms:(3R,4S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-4-hydroxycyclohex-1-enecarbaldehyde

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Chemical Property of (3R,4S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-4-hydroxycyclohex-1-enecarbaldehyde

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Technology Process of (3R,4S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-4-hydroxycyclohex-1-enecarbaldehyde

There total 1 articles about (3R,4S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-4-hydroxycyclohex-1-enecarbaldehyde 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: 91.0%

: 1101867-40-6
(3R,4S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-4-hydroxy-1-hydroxymethylcyclohex-1-ene

: 1101867-41-7
(3R,4S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-4-hydroxycyclohex-1-enecarbaldehyde

Guidance literature:: With manganese(IV) oxide; In dichloromethane; for 16h;
DOI:10.1016/j.bmc.2008.10.053

Reference yield: 28.0%

: 1101867-41-7
(3R,4S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-4-hydroxycyclohex-1-enecarbaldehyde

: 18107-18-1
diazomethyl-trimethyl-silane

: 1101867-42-8
(3R,4S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-1-ethynyl-4-hydroxycyclohex-1-ene

: (3R,4R,5R)-4,5-bis[(tert-butyldimethylsilyl)oxy]-1-ethynyl-3-hydroxy-1-cyclohexene

Guidance literature:: diazomethyl-trimethyl-silane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;

(3R,4S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-4-hydroxycyclohex-1-enecarbaldehyde; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 16h;
DOI:10.1002/ejoc.201601263

Reference yield:

: 1101867-41-7
(3R,4S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-4-hydroxycyclohex-1-enecarbaldehyde

: (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-1-ethynyl-4-oxo-1-cyclohexene

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 0.25 h / -78 °C

1.2: 16 h / -78 - 20 °C

2.1: Dess-Martin periodane / dichloromethane / 20 °C

With n-butyllithium; Dess-Martin periodane; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1002/ejoc.201601263