(S)-1-[(1R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enyl]-but-3-en-2-ol

Base Information

• Chemical Name: (S)-1-[(1R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enyl]-but-3-en-2-ol
• CAS No.: 198336-03-7
• Molecular Formula: C₂₁H₄₀O₂Si
• Molecular Weight: 352.633
• Mol file: 198336-03-7.mol

Synonyms:(S)-1-[(1R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enyl]-but-3-en-2-ol

Chemical Property of (S)-1-[(1R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enyl]-but-3-en-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-[(1R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enyl]-but-3-en-2-ol

There total 16 articles about (S)-1-[(1R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enyl]-but-3-en-2-ol 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:

Methanesulfonic acid 3-[(1R,5R,6R)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-oxiranylmethyl ester → (S)-1-[(1R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enyl]-but-3-en-2-ol (198336-03-7)

Guidance literature:

With sodium naphthalenide; In tetrahydrofuran; at 0 ℃; for 0.166667h; Yield given;

DOI:10.1021/ja973000g

Reference yield:

Methanesulfonic acid (2R,3R)-3-[(1R,5R,6R)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-oxiranylmethyl ester → (S)-1-[(1R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enyl]-but-3-en-2-ol (198336-03-7)

Guidance literature:

With sodium naphthalenide; In tetrahydrofuran; at 0 ℃; for 0.166667h; Yield given;

DOI:10.1021/ja981062g

Reference yield:

(S)-p-mentha-6,8-dien-2-one (2244-16-8,6485-40-1) → (S)-1-[(1R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enyl]-but-3-en-2-ol (198336-03-7)

Guidance literature:

Multi-step reaction with 14 steps

1: H₂O₂, NaOH / methanol / 2 h / 0 °C

2: H₂ / PtO₂ / ethanol / 12 h / 25 °C

3: 1.) LDA / 2.) THF, from -78 to 0 deg C, 2 h

4: Et₃N / CH₂Cl₂ / 12 h

5: 93 percent / L-selectride / tetrahydrofuran / 2 h / -78 °C

6: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

7: sodium naphthalenide / tetrahydrofuran / 0.5 h / 0 °C

8: 74 percent / propionic acid / 72 h / 170 °C

9: 97 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

10: 1.) NaH / 1.) THF, 25 deg C, 30 min, 2.) THF, from 0 to 25 deg C, 5 h

11: 91 percent / DIBAL / CH₂Cl₂ / 2 h / -78 °C

12: 91 percent / diethyl L-tartrate, mol. sieves 4A, Ti(OiPr)4, t-BuOOH / CH₂Cl₂ / 8 h / -20 °C

13: Et₃N / CH₂Cl₂ / 1 h / -20 °C

14: sodium naphthalenide / tetrahydrofuran / 0.17 h / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; diethyl (2R,3R)-tartrate; 4 A molecular sieve; hydrogen; dihydrogen peroxide; L-Selectride; sodium naphthalenide; sodium hydride; diisobutylaluminium hydride; propionic acid; triethylamine; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; methanol; ethanol; dichloromethane;

DOI:10.1021/ja981062g

upstream raw materials:

(1S,4S,6S)-4-Isopropyl-1-methyl-7-oxa-bicyclo[4.1.0]heptan-2-one

(S)-p-mentha-6,8-dien-2-one

(S)-carvone oxide

(1S,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enol

Downstream raw materials:

(1R,2R,6R)-2-[(2S,3S)-3-Hydroxy-2-(4-methoxy-benzyloxy)-3-methyl-pent-4-ynyl]-6-isopropyl-3-methyl-cyclohex-3-enecarbaldehyde

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

(Z)-2-Hydroxymethyl-3-{(1S,2R,6R)-6-isopropyl-2-[(2S,3S)-2-(4-methoxy-benzyloxy)-3-methyl-3-trimethylsilanyloxy-pent-4-ynyl]-3-methyl-cyclohex-3-enyl}-propenal

(E)-2-Cyano-3-{(1S,2R,6R)-2-[(2S,3S)-3-hydroxy-2-(4-methoxy-benzyloxy)-3-methyl-pent-4-ynyl]-6-isopropyl-3-methyl-cyclohex-3-enyl}-acrylic acid ethyl ester