(2R,3R)-3-benzyloxycarbonylamino-4-phenylthio-2-methanesulfonyloxy-1-(4-nitrobenzoyloxy)butane

Base Information

• Chemical Name: (2R,3R)-3-benzyloxycarbonylamino-4-phenylthio-2-methanesulfonyloxy-1-(4-nitrobenzoyloxy)butane
• CAS No.: 188923-26-4
• Molecular Formula: C₂₆H₂₆N₂O₉S₂
• Molecular Weight: 574.632
• Mol file: 188923-26-4.mol

Synonyms:(2R,3R)-3-benzyloxycarbonylamino-4-phenylthio-2-methanesulfonyloxy-1-(4-nitrobenzoyloxy)butane

Chemical Property of (2R,3R)-3-benzyloxycarbonylamino-4-phenylthio-2-methanesulfonyloxy-1-(4-nitrobenzoyloxy)butane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2R,3R)-3-benzyloxycarbonylamino-4-phenylthio-2-methanesulfonyloxy-1-(4-nitrobenzoyloxy)butane

There total 11 articles about (2R,3R)-3-benzyloxycarbonylamino-4-phenylthio-2-methanesulfonyloxy-1-(4-nitrobenzoyloxy)butane 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: 51.0%

4-nitro-benzoyl chloride (122-04-3) + methanesulfonyl chloride (124-63-0) + (2R,3R)-3-benzyloxycarbonylamino-4-phenylthio-1,2-butanediol (188923-25-3) → (2R,3R)-3-benzyloxycarbonylamino-4-phenylthio-2-methanesulfonyloxy-1-(4-nitrobenzoyloxy)butane (188923-26-4)

Guidance literature:

4-nitro-benzoyl chloride; (2R,3R)-3-benzyloxycarbonylamino-4-phenylthio-1,2-butanediol; With triethylamine; In tetrahydrofuran; at 0 - 10 ℃; for 1h;

methanesulfonyl chloride; In tetrahydrofuran; at 0 - 12 ℃; for 1h;

Reference yield:

methanesulfonyl chloride (124-63-0) + 4-Nitro-benzoic acid (2R,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylsulfanyl-butyl ester (1026343-65-6) → (2R,3R)-3-benzyloxycarbonylamino-4-phenylthio-2-methanesulfonyloxy-1-(4-nitrobenzoyloxy)butane (188923-26-4)

Guidance literature:

With triethylamine; In ethyl acetate; for 0.5h;

DOI:10.1021/jo991793e

Reference yield:

benzoic acid (65-85-0,8013-63-6) → (2R,3R)-3-benzyloxycarbonylamino-4-phenylthio-2-methanesulfonyloxy-1-(4-nitrobenzoyloxy)butane (188923-26-4)

Guidance literature:

Multi-step reaction with 7 steps

1: H₂ / Pd/C / propan-2-ol / 9 h / 60 °C

2: K₂CO₃ / toluene; H₂O / 3 h / 20 °C

3: Et₃N / toluene / 1.5 h / 10 °C

4: 1.93 kg / NaOH; Bu₄NBr / toluene; H₂O / 2.5 h / 55 °C

5: aq. HCl / methanol / 3.5 h / Heating

6: 2-picoline / ethyl acetate / 8.5 h / 5 - 10 °C

7: 1.31 kg / Et₃N / ethyl acetate / 0.5 h

With α-picoline; hydrogenchloride; sodium hydroxide; tetrabutylammomium bromide; hydrogen; potassium carbonate; triethylamine; palladium on activated charcoal; In methanol; water; ethyl acetate; isopropyl alcohol; toluene; 1: Hydrogenolysis / 2: Condensation / 3: Condensation / 4: Substitution / 5: Hydrolysis / 6: Esterification / 7: Condensation;

DOI:10.1021/jo991793e

upstream raw materials:

methanesulfonyl chloride

4-Nitro-benzoic acid (2R,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylsulfanyl-butyl ester

4-nitro-benzoyl chloride

benzyl chloroformate

Downstream raw materials:

benzyl [(1R)-1-[(2S)-2-oxiranyl]-2-(phenylsulfanyl)ethyl]carbamate

(3S,4aS,8aS)-N-tert-butyl-2-[(2R,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-(phenylthio)butyl]decahydroisoquinoline-3-carboxamide