(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl N-[(1S,2R)-3-amino-1-benzyl-2-hydroxypropyl]carbamate

Base Information

• Chemical Name: (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl N-[(1S,2R)-3-amino-1-benzyl-2-hydroxypropyl]carbamate
• CAS No.: 288296-23-1
• Molecular Formula: C₁₇H₂₄N₂O₅
• Molecular Weight: 336.388
• Mol file: 288296-23-1.mol

Synonyms:(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl N-[(1S,2R)-3-amino-1-benzyl-2-hydroxypropyl]carbamate

Chemical Property of (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl N-[(1S,2R)-3-amino-1-benzyl-2-hydroxypropyl]carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl N-[(1S,2R)-3-amino-1-benzyl-2-hydroxypropyl]carbamate

There total 6 articles about (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl N-[(1S,2R)-3-amino-1-benzyl-2-hydroxypropyl]carbamate 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: 98.0%

((1S,2R)-3-Azido-1-benzyl-2-hydroxy-propyl)-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester (681028-76-2) → (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl N-[(1S,2R)-3-amino-1-benzyl-2-hydroxypropyl]carbamate (288296-23-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; under 2068.59 Torr;

DOI:10.1016/j.bmcl.2003.12.008

Reference yield:

(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester (98760-08-8,98818-34-9,98818-35-0,103127-56-6,98737-29-2) → (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl N-[(1S,2R)-3-amino-1-benzyl-2-hydroxypropyl]carbamate (288296-23-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / aq. NaN₃ / dimethylformamide / 100 °C

2: 86 percent / TFA / CH₂Cl₂

3: 77 percent / DIEA / acetonitrile

4: 98 percent / H₂ / Pd/C / methanol / 2068.59 Torr

With sodium azide; hydrogen; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.bmcl.2003.12.008

Reference yield:

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol (156928-09-5) → (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl N-[(1S,2R)-3-amino-1-benzyl-2-hydroxypropyl]carbamate (288296-23-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / pyridine / CH₂Cl₂

2: 77 percent / DIEA / acetonitrile

3: 98 percent / H₂ / Pd/C / methanol / 2068.59 Torr

With pyridine; hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; dichloromethane; acetonitrile;

DOI:10.1016/j.bmcl.2003.12.008

upstream raw materials:

((1S,2R)-3-Azido-1-benzyl-2-hydroxy-propyl)-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

[(3S,2R)-3-amino-2-hydroxy-4-phenylbutyl]azide

Downstream raw materials:

[(1S,2R)-1-Benzyl-3-(4-cyano-2,2-dimethyl-butylamino)-2-hydroxy-propyl]-carbamic acid (3R,3aS,6aR)hexahydro-furo[2,3-b]furan-3-yl ester

[(1S,2R)-1-Benzyl-3-(4-dibenzylamino-2,2-dimethyl-butylamino)-2-hydroxy-propyl]-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl N-(1S,2R)-1-benzyl-3-[(3-nitrophenylsulfonyl)(4-cyano-2,2-dimethylbutyl)amino]-2-hydroxypropylcarbamate

(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl N-(1S,2R)-1-benzyl-3-[(4-aminophenylsulfonyl)(5-amino-2,2-dimethylpentyl)amino]-2-hydroxypropylcarbamate