(R)-5-[(S)-2-(Bis-benzyloxy-methyl)-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylmethyl]-2,6,6-trimethyl-3-triisopropylsilanyloxy-cyclohex-2-enone

Base Information

• Chemical Name: (R)-5-[(S)-2-(Bis-benzyloxy-methyl)-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylmethyl]-2,6,6-trimethyl-3-triisopropylsilanyloxy-cyclohex-2-enone
• CAS No.: 226910-54-9
• Molecular Formula: C₄₆H₇₂O₅Si₂
• Molecular Weight: 761.246
• Mol file: 226910-54-9.mol

Synonyms:(R)-5-[(S)-2-(Bis-benzyloxy-methyl)-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylmethyl]-2,6,6-trimethyl-3-triisopropylsilanyloxy-cyclohex-2-enone

Chemical Property of (R)-5-[(S)-2-(Bis-benzyloxy-methyl)-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylmethyl]-2,6,6-trimethyl-3-triisopropylsilanyloxy-cyclohex-2-enone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-5-[(S)-2-(Bis-benzyloxy-methyl)-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylmethyl]-2,6,6-trimethyl-3-triisopropylsilanyloxy-cyclohex-2-enone

There total 12 articles about (R)-5-[(S)-2-(Bis-benzyloxy-methyl)-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylmethyl]-2,6,6-trimethyl-3-triisopropylsilanyloxy-cyclohex-2-enone 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:

triisopropylsilyl chloride (13154-24-0) + 5-[2-(bis-benzyloxy-methyl)-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylmethyl]-3-hydroxy-2,6,6-trimethyl-cyclohex-2-enone → (S)-5-[(S)-2-(Bis-benzyloxy-methyl)-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylmethyl]-2,6,6-trimethyl-3-triisopropylsilanyloxy-cyclohex-2-enone + (R)-5-[(S)-2-(Bis-benzyloxy-methyl)-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylmethyl]-2,6,6-trimethyl-3-triisopropylsilanyloxy-cyclohex-2-enone (226910-54-9)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 0 ℃; for 4h; Yield given; Yields of byproduct given;

DOI:10.1021/ja984250f

Reference yield:

3,4-epoxyhex-1-ene (34485-78-4) → (R)-5-[(S)-2-(Bis-benzyloxy-methyl)-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylmethyl]-2,6,6-trimethyl-3-triisopropylsilanyloxy-cyclohex-2-enone (226910-54-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) t-BuLi, 2.) CuCN, 4.) PDC, 4A molecular sieves

2: 1.) LDA / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, from -78 deg C to 5 deg C, 7 h

3: t-BuOK / tetrahydrofuran / 1 h / 0 °C

4: Et₃N / tetrahydrofuran / 4 h / 0 °C

With dipyridinium dichromate; 4 A molecular sieve; potassium tert-butylate; tert.-butyl lithium; triethylamine; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/ja984250f

Reference yield:

3-isobutoxycyclohex-2-en-1-one (23074-59-1) → (R)-5-[(S)-2-(Bis-benzyloxy-methyl)-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylmethyl]-2,6,6-trimethyl-3-triisopropylsilanyloxy-cyclohex-2-enone (226910-54-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 93 percent / NBS / 1,2-dichloro-ethane / 3 h / 0 °C

2: 1.) TMEDA, n-BuLi / 1.) THF, hexane, -78 deg C, 2 h, 2.) THF, hexane, -78 deg C, 1 h

3: 76 percent / CuO, CuCl₂ / acetonitrile / 4 h / 40 °C

4: chiral oxazaborolidine, BH₃*SMe₂ / tetrahydrofuran; toluene / 2 h / -23 - 0 °C

5: imidazole / dimethylformamide / Ambient temperature

6: 1.) t-BuLi, 2.) CuCN, 4.) PDC, 4A molecular sieves

7: 1.) LDA / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, from -78 deg C to 5 deg C, 7 h

8: t-BuOK / tetrahydrofuran / 1 h / 0 °C

9: Et₃N / tetrahydrofuran / 4 h / 0 °C

With 1H-imidazole; N-Bromosuccinimide; dipyridinium dichromate; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; dimethylsulfide borane complex; 4 A molecular sieve; chiral oxazaborolidine; potassium tert-butylate; tert.-butyl lithium; triethylamine; copper(II) oxide; copper dichloride; lithium diisopropyl amide; In tetrahydrofuran; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/ja984250f

upstream raw materials:

triisopropylsilyl chloride

3,4-epoxyhex-1-ene

3-isobutoxycyclohex-2-en-1-one

1,3-cylohexanedione

Downstream raw materials:

(R)-1-Benzyloxymethyl-5-[(S)-2-(bis-benzyloxy-methyl)-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylmethyl]-2,6,6-trimethyl-3-triisopropylsilanyloxy-cyclohex-2-enol