2-[(2R,3R,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-3-[(1S,2R,3R)-2-((S)-cyano-methyl-methyl)-3-methyl-cyclohexyl]-3-hydroxy-propionic acid methyl ester

Base Information

• Chemical Name: 2-[(2R,3R,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-3-[(1S,2R,3R)-2-((S)-cyano-methyl-methyl)-3-methyl-cyclohexyl]-3-hydroxy-propionic acid methyl ester
• CAS No.: 130517-71-4
• Molecular Formula: C₂₇H₄₉NO₅Si
• Molecular Weight: 495.775
• Mol file: 130517-71-4.mol

Synonyms:

Chemical Property of 2-[(2R,3R,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-3-[(1S,2R,3R)-2-((S)-cyano-methyl-methyl)-3-methyl-cyclohexyl]-3-hydroxy-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(2R,3R,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-3-[(1S,2R,3R)-2-((S)-cyano-methyl-methyl)-3-methyl-cyclohexyl]-3-hydroxy-propionic acid methyl ester

There total 3 articles about 2-[(2R,3R,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-3-[(1S,2R,3R)-2-((S)-cyano-methyl-methyl)-3-methyl-cyclohexyl]-3-hydroxy-propionic acid methyl ester 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:

(S)-2-[(1R,2S,6R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-6-methyl-cyclohexyl]-propionitrile (130607-96-4) → 2-[(2R,3R,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-3-[(1S,2R,3R)-2-((S)-cyano-methyl-methyl)-3-methyl-cyclohexyl]-3-hydroxy-propionic acid methyl ester (130517-71-4)

Guidance literature:

Multi-step reaction with 3 steps

1: HF / acetonitrile; H₂O

2: Swern oxidation

3: 1.) lithium diisopropylamide / 1.) THF, -100 deg C, 15 min, 2.) 15 min

With hydrogen fluoride; lithium diisopropyl amide; In water; acetonitrile;

DOI:10.1248/cpb.38.1784

Reference yield:

(S)-2-((1R,2S,6R)-2-Hydroxymethyl-6-methyl-cyclohexyl)-propionitrile (148766-02-3) → 2-[(2R,3R,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-3-[(1S,2R,3R)-2-((S)-cyano-methyl-methyl)-3-methyl-cyclohexyl]-3-hydroxy-propionic acid methyl ester (130517-71-4)

Guidance literature:

Multi-step reaction with 2 steps

1: Swern oxidation

2: 1.) lithium diisopropylamide / 1.) THF, -100 deg C, 15 min, 2.) 15 min

With lithium diisopropyl amide;

DOI:10.1248/cpb.38.1784

Reference yield:

(S)-2-((1R,2S,6R)-2-Formyl-6-methyl-cyclohexyl)-propionitrile (130517-70-3) + [(2S,3R,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-acetic acid methyl ester (125011-00-9) → 2-[(2R,3R,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-3-[(1S,2R,3R)-2-((S)-cyano-methyl-methyl)-3-methyl-cyclohexyl]-3-hydroxy-propionic acid methyl ester (130517-71-4)

Guidance literature:

With lithium diisopropyl amide; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, -100 deg C, 15 min, 2.) 15 min;

DOI:10.1248/cpb.38.1784

upstream raw materials:

(S)-2-((1R,2S,6R)-2-Formyl-6-methyl-cyclohexyl)-propionitrile

[(2S,3R,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-acetic acid methyl ester

(S)-2-((1R,2S,6R)-2-Hydroxymethyl-6-methyl-cyclohexyl)-propionitrile

(S)-2-[(1R,2S,6R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-6-methyl-cyclohexyl]-propionitrile

Downstream raw materials:

(E)-2-[(2R,3R,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-3-[(1S,2S,3R)-2-((S)-cyano-methyl-methyl)-3-methyl-cyclohexyl]-acrylic acid methyl ester

(Z)-2-[(2R,3R,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-3-[(1S,2S,3R)-2-((S)-cyano-methyl-methyl)-3-methyl-cyclohexyl]-acrylic acid methyl ester