(4S,6R)-6-((Z)-(S)-3-Benzyloxymethyl-1-methyl-pent-1-enyl)-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-one

Base Information

• Chemical Name: (4S,6R)-6-((Z)-(S)-3-Benzyloxymethyl-1-methyl-pent-1-enyl)-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-one
• CAS No.: 616207-90-0
• Molecular Formula: C₃₅H₄₄O₄Si
• Molecular Weight: 556.817
• Mol file: 616207-90-0.mol

Synonyms:(4S,6R)-6-((Z)-(S)-3-Benzyloxymethyl-1-methyl-pent-1-enyl)-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-one

Chemical Property of (4S,6R)-6-((Z)-(S)-3-Benzyloxymethyl-1-methyl-pent-1-enyl)-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,6R)-6-((Z)-(S)-3-Benzyloxymethyl-1-methyl-pent-1-enyl)-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-one

There total 11 articles about (4S,6R)-6-((Z)-(S)-3-Benzyloxymethyl-1-methyl-pent-1-enyl)-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-one 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: 100.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (4S,6R)-6-((Z)-(S)-3-Benzyloxymethyl-1-methyl-pent-1-enyl)-4-hydroxy-tetrahydro-pyran-2-one (616207-89-7) → (4S,6R)-6-((Z)-(S)-3-Benzyloxymethyl-1-methyl-pent-1-enyl)-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-one (616207-90-0)

Guidance literature:

With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 23 ℃; for 13h;

DOI:10.1016/j.tetlet.2003.08.023

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → (4S,6R)-6-((Z)-(S)-3-Benzyloxymethyl-1-methyl-pent-1-enyl)-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-one (616207-90-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 80 percent / TiCl₄; Et₃N / CH₂Cl₂ / 1.5 h / 0 °C

2.1: 94 percent / LiBH₄ / methanol; tetrahydrofuran / 1 h / 23 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.75 h / -60 °C

4.1: NaH / tetrahydrofuran / 2 h / -78 - -20 °C

5.1: 96 percent / Dibal-H / CH₂Cl₂ / 1 h / -78 - -40 °C

6.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1.5 h / 23 °C

7.1: diethyl ether / 3 h / -80 °C

8.1: 77 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

9.1: 83 percent / Cl₂(Pcy)2Ru=CHPh / CH₂Cl₂ / 12 h / 40 °C

10.1: H₂O₂; aq. NaOH / methanol / 1.5 h

10.2: 74 percent / NaBH₄; PhSeSePh; AcOH / propan-2-ol / 0.5 h / 0 °C

11.1: 100 percent / imidazole; DMAP / dimethylformamide / 13 h / 23 °C

With 1H-imidazole; dmap; sodium hydroxide; lithium borohydride; oxalyl dichloride; dihydrogen peroxide; titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; Grubbs catalyst first generation; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 3.1: Swern oxidation / 4.1: Horner-Emmons reaction;

DOI:10.1016/j.tetlet.2003.08.023

Reference yield:

2-<(benzyloxy)-methyl>butyraldehyde (916501-75-2) → (4S,6R)-6-((Z)-(S)-3-Benzyloxymethyl-1-methyl-pent-1-enyl)-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-one (616207-90-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: NaH / tetrahydrofuran / 2 h / -78 - -20 °C

2.1: 96 percent / Dibal-H / CH₂Cl₂ / 1 h / -78 - -40 °C

3.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1.5 h / 23 °C

4.1: diethyl ether / 3 h / -80 °C

5.1: 77 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

6.1: 83 percent / Cl₂(Pcy)2Ru=CHPh / CH₂Cl₂ / 12 h / 40 °C

7.1: H₂O₂; aq. NaOH / methanol / 1.5 h

7.2: 74 percent / NaBH₄; PhSeSePh; AcOH / propan-2-ol / 0.5 h / 0 °C

8.1: 100 percent / imidazole; DMAP / dimethylformamide / 13 h / 23 °C

With 1H-imidazole; dmap; sodium hydroxide; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; Grubbs catalyst first generation; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1.1: Horner-Emmons reaction;

DOI:10.1016/j.tetlet.2003.08.023

upstream raw materials:

tert-butylchlorodiphenylsilane

(4S,6R)-6-((Z)-(S)-3-Benzyloxymethyl-1-methyl-pent-1-enyl)-4-hydroxy-tetrahydro-pyran-2-one

Benzyloxymethyl chloride

2-<(benzyloxy)-methyl>butyraldehyde

Downstream raw materials:

(Z)-(3S,5R,8S)-8-Benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-6-methyl-dec-6-enoic acid methoxy-methyl-amide

(Z)-(3S,5R,8S)-8-Benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-5-(2-methoxy-ethoxymethoxy)-6-methyl-dec-6-enoic acid methoxy-methyl-amide