[(R)-1-Benzenesulfonyl-2-((2S,3S,5R,6S)-6-ethoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-1-phenylselanyl-propyl]-trimethyl-silane

Base Information

• Chemical Name: [(R)-1-Benzenesulfonyl-2-((2S,3S,5R,6S)-6-ethoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-1-phenylselanyl-propyl]-trimethyl-silane
• CAS No.: 81309-99-1
• Molecular Formula: C₂₇H₄₀O₄SSeSi
• Molecular Weight: 567.724
• Mol file: 81309-99-1.mol

Synonyms:

Chemical Property of [(R)-1-Benzenesulfonyl-2-((2S,3S,5R,6S)-6-ethoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-1-phenylselanyl-propyl]-trimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(R)-1-Benzenesulfonyl-2-((2S,3S,5R,6S)-6-ethoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-1-phenylselanyl-propyl]-trimethyl-silane

There total 7 articles about [(R)-1-Benzenesulfonyl-2-((2S,3S,5R,6S)-6-ethoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-1-phenylselanyl-propyl]-trimethyl-silane 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:

ethyl 2,3,4-trideoxy-4-C-methyl-2-C-methylene-α-D-erythro-hexopyranoside (81309-96-8) → [(R)-1-Benzenesulfonyl-2-((2S,3S,5R,6S)-6-ethoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-1-phenylselanyl-propyl]-trimethyl-silane (81309-99-1)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / Pd/C / ethyl acetate

2: 1.) (COCl)2, Et₃N 2.) MCPBA / 1.) DMSO

3: 1.) THF, -78 deg C, 5 min.

With oxalyl dichloride; hydrogen; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In ethyl acetate;

DOI:10.1016/S0040-4039(01)82936-1

Reference yield:

Benzoic acid (2S,3S,6S)-6-ethoxy-3-methyl-5-oxo-tetrahydro-pyran-2-ylmethyl ester (81309-95-7) → [(R)-1-Benzenesulfonyl-2-((2S,3S,5R,6S)-6-ethoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-1-phenylselanyl-propyl]-trimethyl-silane (81309-99-1)

Guidance literature:

Multi-step reaction with 4 steps

1: dimethylsulfoxide / 48 h / 50 °C

2: H₂ / Pd/C / ethyl acetate

3: 1.) (COCl)2, Et₃N 2.) MCPBA / 1.) DMSO

4: 1.) THF, -78 deg C, 5 min.

With oxalyl dichloride; hydrogen; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In dimethyl sulfoxide; ethyl acetate;

DOI:10.1016/S0040-4039(01)82936-1

Reference yield:

Benzoic acid (2R,3R,6S)-6-ethoxy-3-hydroxy-3-methyl-3,6-dihydro-2H-pyran-2-ylmethyl ester (81309-93-5) → [(R)-1-Benzenesulfonyl-2-((2S,3S,5R,6S)-6-ethoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-1-phenylselanyl-propyl]-trimethyl-silane (81309-99-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 35 percent / CrO₃, H₂SO₄

2: H₂ / Pd/C

3: dimethylsulfoxide / 48 h / 50 °C

4: H₂ / Pd/C / ethyl acetate

5: 1.) (COCl)2, Et₃N 2.) MCPBA / 1.) DMSO

6: 1.) THF, -78 deg C, 5 min.

With chromium(VI) oxide; oxalyl dichloride; sulfuric acid; hydrogen; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In dimethyl sulfoxide; ethyl acetate;

DOI:10.1016/S0040-4039(01)82936-1

upstream raw materials:

Phenylselenyl chloride

methyllithium

[(Z)-1-Benzenesulfonyl-2-((2S,3S,5R,6S)-6-ethoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-vinyl]-trimethyl-silane

ethyl 2,3,4-trideoxy-4-C-methyl-2-C-methylene-α-D-erythro-hexopyranoside

Downstream raw materials:

(+)-Prelog-Djerassi lactonic acid