((1S,2R)-1-Benzyl-3,3-difluoro-2-hydroxy-5-phenyl-pent-4-ynyl)-carbamic acid tert-butyl ester

Base Information

• Chemical Name: ((1S,2R)-1-Benzyl-3,3-difluoro-2-hydroxy-5-phenyl-pent-4-ynyl)-carbamic acid tert-butyl ester
• CAS No.: 147770-25-0
• Molecular Formula: C₂₃H₂₅F₂NO₃
• Molecular Weight: 401.453

Synonyms:((1S,2R)-1-Benzyl-3,3-difluoro-2-hydroxy-5-phenyl-pent-4-ynyl)-carbamic acid tert-butyl ester

Chemical Property of ((1S,2R)-1-Benzyl-3,3-difluoro-2-hydroxy-5-phenyl-pent-4-ynyl)-carbamic acid tert-butyl ester

Chemical Property:

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Technology Process of ((1S,2R)-1-Benzyl-3,3-difluoro-2-hydroxy-5-phenyl-pent-4-ynyl)-carbamic acid tert-butyl ester

There total 2 articles about ((1S,2R)-1-Benzyl-3,3-difluoro-2-hydroxy-5-phenyl-pent-4-ynyl)-carbamic acid tert-butyl 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: 21.0%

Boc-L-phenylalaninal (72155-45-4) + bromodifluoromethylphenylacetylene (82477-43-8) → ((1S,2R)-1-Benzyl-3,3-difluoro-2-hydroxy-5-phenyl-pent-4-ynyl)-carbamic acid tert-butyl ester (147770-25-0) + ((1S,2S)-1-Benzyl-3,3-difluoro-2-hydroxy-5-phenyl-pent-4-ynyl)-carbamic acid tert-butyl ester (147770-21-6)

Guidance literature:

With mercury dichloride; zinc; In tetrahydrofuran; for 0.5h; Ambient temperature; sonification;

DOI:10.1016/0022-1139(94)03223-M

Reference yield:

(S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol (66605-57-0) → ((1S,2R)-1-Benzyl-3,3-difluoro-2-hydroxy-5-phenyl-pent-4-ynyl)-carbamic acid tert-butyl ester (147770-25-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) DMSO, oxalyl chloride, 2.) NEt₃ / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) -78 deg C, 25 min

2: 32 percent / Zn dust, HgCl₂ / tetrahydrofuran / 0.5 h / Ambient temperature; sonification

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; mercury dichloride; zinc; In tetrahydrofuran;

DOI:10.1016/0022-1139(94)03223-M

Reference yield: 96.0%

((1S,2R)-1-Benzyl-3,3-difluoro-2-hydroxy-5-phenyl-pent-4-ynyl)-carbamic acid tert-butyl ester (147770-25-0) → N-t-butyloxycarbonyl-(1,6-diphenyl-3,3-difluoro-4(R,S)-hydroxy-5(S)-amino-hexane) (147770-26-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 1h;

DOI:10.1016/0022-1139(94)03223-M

upstream raw materials:

Boc-L-phenylalaninal

bromodifluoromethylphenylacetylene

(S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol

Downstream raw materials:

N-t-butyloxycarbonyl-(1,6-diphenyl-3,3-difluoro-4(R,S)-hydroxy-5(S)-amino-hexane)

2S-(N-Benzyloxycarbonyl-valinyl)amino-3-oxo-4,4-difluoro-1,6-diphenyl-hexane

(2S,3R)-2-Amino-4,4-difluoro-1,6-diphenyl-hexan-3-ol

[(S)-1-((1S,2R)-1-Benzyl-3,3-difluoro-2-hydroxy-5-phenyl-pentylcarbamoyl)-2-methyl-propyl]-carbamic acid benzyl ester

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