Benzoic acid (2R,3S,4S,5S)-5-bromo-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,4S,5S)-5-bromo-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-tetrahydro-pyran-4-yl ester
• CAS No.: 206654-16-2
• Molecular Formula: C₁₉H₂₉BrO₅Si
• Molecular Weight: 445.426

Synonyms:Benzoic acid (2R,3S,4S,5S)-5-bromo-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-tetrahydro-pyran-4-yl ester

Chemical Property of Benzoic acid (2R,3S,4S,5S)-5-bromo-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-tetrahydro-pyran-4-yl ester

Chemical Property:

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Technology Process of Benzoic acid (2R,3S,4S,5S)-5-bromo-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-tetrahydro-pyran-4-yl ester

There total 1 articles about Benzoic acid (2R,3S,4S,5S)-5-bromo-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-tetrahydro-pyran-4-yl ester 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:

tert-Butyl-((3aR,6R,7S,7aR)-6-methoxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy)-dimethyl-silane → Benzoic acid (2R,3S,4S,5S)-5-bromo-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-tetrahydro-pyran-4-yl ester (206654-16-2)

Guidance literature:

With Bromotrichloromethane; In tetrachloromethane; for 5h; Ambient temperature; Irradiation;

DOI:10.1002/hlca.19980810323

Reference yield: 81.0%

Benzoic acid (2R,3S,4S,5S)-5-bromo-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-tetrahydro-pyran-4-yl ester (206654-16-2) → Benzoic acid (2R,3S,4R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-tetrahydro-pyran-4-yl ester

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; at 60 ℃; for 3h;

DOI:10.1002/hlca.19980810323

Reference yield:

Benzoic acid (2R,3S,4S,5S)-5-bromo-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-tetrahydro-pyran-4-yl ester (206654-16-2) → Benzoic acid (2R,3R,4R)-2-allyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-4-yl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / Bu₃SnH, AIBN / 3 h / 60 °C

2: 21 percent / Me₃SiOTf / acetonitrile / 72 h / Ambient temperature

With 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tri-n-butyl-tin hydride; In acetonitrile;

DOI:10.1002/hlca.19980810323

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