(R)-3-[(1S,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-2-methyl-propionaldehyde

Base Information

• Chemical Name: (R)-3-[(1S,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-2-methyl-propionaldehyde
• CAS No.: 131719-86-3
• Molecular Formula: C₁₇H₃₄O₃Si
• Molecular Weight: 314.541
• Mol file: 131719-86-3.mol

Synonyms:(R)-3-[(1S,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-2-methyl-propionaldehyde

Chemical Property of (R)-3-[(1S,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-2-methyl-propionaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-[(1S,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-2-methyl-propionaldehyde

There total 8 articles about (R)-3-[(1S,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-2-methyl-propionaldehyde 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: 51.0%

C55H96O9Si2 (1156545-78-6) → (3R,6S)-6-((S)-2-Methoxy-3-oxo-butyl)-3-methyl-tetrahydro-pyran-2-one (131719-88-5) + (R)-3-[(1S,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-2-methyl-propionaldehyde (131719-86-3)

Guidance literature:

C₅₅H₉₆O₉Si₂; With ozone; In dichloromethane; at -78 ℃;

With dimethylsulfide; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1002/chem.200801656

Reference yield:

(R)-4-Benzyl-3-{3-[(1S,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-2-methyl-propionyl}-oxazolidin-2-one → (R)-3-[(1S,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-2-methyl-propionaldehyde (131719-86-3)

Guidance literature:

With lithium aluminium tetrahydride; sodium acetate; pyridinium chlorochromate; Yield given. Multistep reaction; 1.) Et₂O, 0 deg C;

DOI:10.1021/ja00075a092

Reference yield:

(R)-4-Benzyl-3-{3-[(1S,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-propionyl}-oxazolidin-2-one → (R)-3-[(1S,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-2-methyl-propionaldehyde (131719-86-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaHMDS / 1.) THF, -78 deg C, 2.) THF

2: 1.) LAH, 2.) PCC, NaOAc / 1.) Et₂O, 0 deg C

With lithium aluminium tetrahydride; sodium acetate; sodium hexamethyldisilazane; pyridinium chlorochromate;

DOI:10.1021/ja00075a092

upstream raw materials:

(3E,6E)-(R)-9-[(1S,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-4,8-dimethyl-5-oxo-nona-3,6-dienoic acid methyl ester

C₄₁H₆₉NO₁₂Si

C₄₄H₇₃NO₁₃Si

(22E,24E,26E,27E,29R,30S,31R,32R,34S,36S,38S,39S,40S,41R,50R)-40,50-dihydroxy-39-[(1R)-2-[(1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl]-1-methyl-ethyl]-38,41-dimethoxy-29,30,31,32,42,43-hexamethyl-60,61-dioxa-51-azatricyclohexatriaconta-22,24,26⁽⁴²⁾,27⁽⁴³⁾-tetraene-44,45,46,47,48-pentone

Downstream raw materials:

(2R,3S)-1-[(1S,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-2-methyl-hex-5-en-3-ol

(S)-Piperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-[(1R,2R)-3-[(1S,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-2-methyl-1-((S)-1-methyl-2-oxo-ethyl)-propyl] ester

(S)-Piperidine-2-carboxylic acid (1R,2S,3S)-6-allyl-3-(tert-butyl-dimethyl-silanyloxy)-1-{(R)-2-[(1S,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-1-methyl-ethyl}-2-methyl-5-oxo-non-8-enyl ester

C₆₀H₁₀₉NO₁₁Si₃