(+)-(1S,2S,3R,4S)-5-chloro-3-exo-hydroxy-3-endo-<(tert-butyl)dimethylsilyloxy>-7-oxabicyclo<2.2.1>hept-5-en-2-exo-yl metachlorobenzoate

Base Information

• Chemical Name: (+)-(1S,2S,3R,4S)-5-chloro-3-exo-hydroxy-3-endo-<(tert-butyl)dimethylsilyloxy>-7-oxabicyclo<2.2.1>hept-5-en-2-exo-yl metachlorobenzoate
• CAS No.: 128503-25-3
• Molecular Formula: C₁₉H₂₄Cl₂O₅Si
• Molecular Weight: 431.388
• Mol file: 128503-25-3.mol

Synonyms:(+)-(1S,2S,3R,4S)-5-chloro-3-exo-hydroxy-3-endo-<(tert-butyl)dimethylsilyloxy>-7-oxabicyclo<2.2.1>hept-5-en-2-exo-yl metachlorobenzoate

Chemical Property of (+)-(1S,2S,3R,4S)-5-chloro-3-exo-hydroxy-3-endo-<(tert-butyl)dimethylsilyloxy>-7-oxabicyclo<2.2.1>hept-5-en-2-exo-yl metachlorobenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(1S,2S,3R,4S)-5-chloro-3-exo-hydroxy-3-endo-<(tert-butyl)dimethylsilyloxy>-7-oxabicyclo<2.2.1>hept-5-en-2-exo-yl metachlorobenzoate

There total 5 articles about (+)-(1S,2S,3R,4S)-5-chloro-3-exo-hydroxy-3-endo-<(tert-butyl)dimethylsilyloxy>-7-oxabicyclo<2.2.1>hept-5-en-2-exo-yl metachlorobenzoate 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: 69.0%

(-)-(1S,4R,5R,6R)-5-exo-benzeneselenyl-2-<(tert-butyl)dimethylsilyloxy>-6-endo-chloro-7-oxabicyclo<2.2.1>hept-2-ene (128530-72-3) + 3-chloro-benzenecarboperoxoic acid (937-14-4) → (+)-(1S,2S,3R,4S)-5-chloro-3-exo-hydroxy-3-endo-<(tert-butyl)dimethylsilyloxy>-7-oxabicyclo<2.2.1>hept-5-en-2-exo-yl metachlorobenzoate (128503-25-3)

Guidance literature:

With sodium acetate; In dichloromethane; at 0 - 20 ℃; for 0.5h;

DOI:10.1016/S0040-4039(00)70712-X

Reference yield:

(+)-(1R,4R)-7-oxabicyclo<2.2.1>-hept-5-en-2-one (88708-22-9) → (+)-(1S,2S,3R,4S)-5-chloro-3-exo-hydroxy-3-endo-<(tert-butyl)dimethylsilyloxy>-7-oxabicyclo<2.2.1>hept-5-en-2-exo-yl metachlorobenzoate (128503-25-3)

Guidance literature:

Multi-step reaction with 3 steps

2: 95 percent / Et₃N / dimethylformamide / 40 °C

3: 69 percent / AcONa / CH₂Cl₂ / a) 0 deg C, 5 min., b) 20 deg C, 30 min.

With sodium acetate; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)88357-5

Reference yield:

N-methyl-N-tert-butyldimethylsilyl-1,1,1-trifluoroacetamide (77377-52-7) → (+/-)-(1RS,2RS,3SR,4SR)-5-chloro-3-exo-hydroxy-3-endo-<(tert-butyl)dimethylsilyloxy>-7-oxabicyclo<2.2.1>hept-5-en-2-exo-yl metachlorobenzoate (128503-25-3,146388-99-0)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / dimethylformamide / 40 °C

2: AcONa / CH₂Cl₂ / a) 0 deg C, 5 min., b) 20 deg C, 30 min.

With sodium acetate; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)88357-5

upstream raw materials:

(-)-(1S,4R,5R,6R)-5-exo-benzeneselenyl-2-<(tert-butyl)dimethylsilyloxy>-6-endo-chloro-7-oxabicyclo<2.2.1>hept-2-ene

3-chloro-benzenecarboperoxoic acid

(+)-(1R,4R)-7-oxabicyclo<2.2.1>-hept-5-en-2-one

(+/-)-(1RS,4SR,5SR,6SR)-5-exo-benzeneselenyl-2-<(tert-butyl)dimethylsilyloxy>-6-endo-chloro-7-oxabicyclo<2.2.1>hept-2-ene

Downstream raw materials:

(-)-(1S,4S,5S,7S)-7-endo-chloro-3-oxo-2,8-dioxabicyclo<3.2.1>oct-4-exo-yl metachlorobenzoate

(1S,2S,3S,4S,5S)-5-endo-chloro-3-exo-hydroxy-3-endo-<(tert-butyl)dimethylsilyloxy>-7-oxabicyclo<2.2.1>hept-2-exo-yl metachlorobenzoate

(1S,3S,4S,5S)-5-endo-chloro-3-oxo-7-oxabicyclo<2.2.1>hept-2-exo-yl metachlorobenzoate

3-Chloro-benzoic acid (S)-((2S,4S)-4-chloro-5-hydroxy-tetrahydro-furan-2-yl)-methoxycarbonyl-methyl ester