1-[(1R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enyl]-3-methyl-pent-4-yne-2,3-diol

Base Information

• Chemical Name: 1-[(1R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enyl]-3-methyl-pent-4-yne-2,3-diol
• CAS No.: 201142-31-6
• Molecular Formula: C₂₃H₄₂O₃Si
• Molecular Weight: 394.67
• Mol file: 201142-31-6.mol

Synonyms:1-[(1R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enyl]-3-methyl-pent-4-yne-2,3-diol

Chemical Property of 1-[(1R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enyl]-3-methyl-pent-4-yne-2,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(1R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enyl]-3-methyl-pent-4-yne-2,3-diol

There total 3 articles about 1-[(1R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enyl]-3-methyl-pent-4-yne-2,3-diol 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: 76.0%

4-[(1R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enyl]-3-hydroxy-butan-2-one (201142-29-2) + acetylenemagnesium bromide (4301-14-8) → 1-[(1R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enyl]-3-methyl-pent-4-yne-2,3-diol (201142-31-6)

Guidance literature:

In tetrahydrofuran; at -78 - -20 ℃; for 14h;

DOI:10.1002/anie.199725201

Reference yield:

(1R,5R,6R)-2-[6-(tert-butyldimethylsilanyloxymethyl)-5-isopropyl-2-methylcyclohex-2-enyl]acetaldehyde (198336-00-4) → 1-[(1R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enyl]-3-methyl-pent-4-yne-2,3-diol (201142-31-6)

Guidance literature:

Multi-step reaction with 3 steps

1: tert-BuLi / tetrahydrofuran / 1.) -78 to 0 deg C, 1 h, 2.) -78 to -40 deg C

2: conc. H₂SO₄ / diethyl ether / 0.03 h / 25 °C

3: 76 percent / tetrahydrofuran / 14 h / -78 - -20 °C

With sulfuric acid; tert.-butyl lithium; In tetrahydrofuran; diethyl ether;

DOI:10.1002/anie.199725201

Reference yield:

1-[(1R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enyl]-3-ethoxy-but-3-en-2-ol → 1-[(1R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enyl]-3-methyl-pent-4-yne-2,3-diol (201142-31-6)

Guidance literature:

Multi-step reaction with 2 steps

1: conc. H₂SO₄ / diethyl ether / 0.03 h / 25 °C

2: 76 percent / tetrahydrofuran / 14 h / -78 - -20 °C

With sulfuric acid; In tetrahydrofuran; diethyl ether;

DOI:10.1002/anie.199725201

upstream raw materials:

4-[(1R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enyl]-3-hydroxy-butan-2-one

acetylenemagnesium bromide

(1R,5R,6R)-2-[6-(tert-butyldimethylsilanyloxymethyl)-5-isopropyl-2-methylcyclohex-2-enyl]acetaldehyde

Downstream raw materials:

[(1R,2R,6R)-6-Isopropyl-3-methyl-2-((2S,3S)-3-methyl-2,3-bis-triethylsilanyloxy-pent-4-ynyl)-cyclohex-3-enyl]-methanol

(1R,2R,6R)-6-Isopropyl-3-methyl-2-((2S,3S)-3-methyl-2,3-bis-triethylsilanyloxy-pent-4-ynyl)-cyclohex-3-enecarbaldehyde

(4R,5R,6R)-4-Isopropyl-1-methyl-6-((2S,3S)-3-methyl-2,3-bis-triethylsilanyloxy-pent-4-ynyl)-5-triethylsilanyloxymethyl-cyclohexene

(Z)-2-Hydroxymethyl-3-[(1S,2R,6R)-6-isopropyl-3-methyl-2-((2S,3S)-3-methyl-2,3-bis-triethylsilanyloxy-pent-4-ynyl)-cyclohex-3-enyl]-propenal