(1S,3R,9R,10S)-9-[(2R,3S,4S,5R,6R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-3-methyl-4,11-dioxa-bicyclo[8.1.0]undecane-5,7-dione

Base Information

• Chemical Name: (1S,3R,9R,10S)-9-[(2R,3S,4S,5R,6R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-3-methyl-4,11-dioxa-bicyclo[8.1.0]undecane-5,7-dione
• CAS No.: 212895-32-4
• Molecular Formula: C₃₄H₅₆O₈SeSi₂
• Molecular Weight: 727.945

Synonyms:(1S,3R,9R,10S)-9-[(2R,3S,4S,5R,6R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-3-methyl-4,11-dioxa-bicyclo[8.1.0]undecane-5,7-dione

Chemical Property of (1S,3R,9R,10S)-9-[(2R,3S,4S,5R,6R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-3-methyl-4,11-dioxa-bicyclo[8.1.0]undecane-5,7-dione

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Technology Process of (1S,3R,9R,10S)-9-[(2R,3S,4S,5R,6R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-3-methyl-4,11-dioxa-bicyclo[8.1.0]undecane-5,7-dione

There total 5 articles about (1S,3R,9R,10S)-9-[(2R,3S,4S,5R,6R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-3-methyl-4,11-dioxa-bicyclo[8.1.0]undecane-5,7-dione 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: 92.0%

decarestrictine B (127393-91-3) + Acetic acid (2R,3S,4S,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yl ester (212895-31-3) → (1S,3R,9R,10S)-9-[(2R,3S,4S,5R,6R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-3-methyl-4,11-dioxa-bicyclo[8.1.0]undecane-5,7-dione (212895-32-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In diethyl ether; 1.) -78 deg C, 15 min, 2.) -25 deg C, 30 min;

DOI:10.1002/(SICI)1521-3765(19980710)4:7<1324::AID-CHEM1324>3.0.CO;2-6

Reference yield:

Phenylselenyl chloride (5707-04-0) → (1S,3R,9R,10S)-9-[(2R,3S,4S,5R,6R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-3-methyl-4,11-dioxa-bicyclo[8.1.0]undecane-5,7-dione (212895-32-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 4 Angstroem molecular sieves / toluene / 12 h

2: 92 percent / TMSOTf / diethyl ether / 1.) -78 deg C, 15 min, 2.) -25 deg C, 30 min

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In diethyl ether; toluene;

DOI:10.1002/(SICI)1521-3765(19980710)4:7<1324::AID-CHEM1324>3.0.CO;2-6

Reference yield:

3,4-bis-(tert-butyldimethylsilyl)-1,5-anhydro-2,6-dideoxy-D-arabino-hex-1-enitol (129830-33-7) → (1S,3R,9R,10S)-9-[(2R,3S,4S,5R,6R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yloxy]-3-methyl-4,11-dioxa-bicyclo[8.1.0]undecane-5,7-dione (212895-32-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 4 Angstroem molecular sieves / toluene / 12 h

2: 92 percent / TMSOTf / diethyl ether / 1.) -78 deg C, 15 min, 2.) -25 deg C, 30 min

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In diethyl ether; toluene;

DOI:10.1002/(SICI)1521-3765(19980710)4:7<1324::AID-CHEM1324>3.0.CO;2-6

upstream raw materials:

decarestrictine B

Acetic acid (2R,3S,4S,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yl ester

Phenylselenyl chloride

3,4-bis-(tert-butyldimethylsilyl)-1,5-anhydro-2,6-dideoxy-D-arabino-hex-1-enitol

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