dl-(1β,2α,3β,5β)-2-(hydroxyethyl)-3-<(phenylsulfonyl)amino>-6-oxabicyclo<3.1.0>hexane

Base Information

• Chemical Name: dl-(1β,2α,3β,5β)-2-(hydroxyethyl)-3-<(phenylsulfonyl)amino>-6-oxabicyclo<3.1.0>hexane
• CAS No.: 113084-34-7
• Molecular Formula: C₁₃H₁₇NO₄S
• Molecular Weight: 283.348
• Mol file: 113084-34-7.mol

Synonyms:dl-(1β,2α,3β,5β)-2-(hydroxyethyl)-3-<(phenylsulfonyl)amino>-6-oxabicyclo<3.1.0>hexane

Chemical Property of dl-(1β,2α,3β,5β)-2-(hydroxyethyl)-3-<(phenylsulfonyl)amino>-6-oxabicyclo<3.1.0>hexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dl-(1β,2α,3β,5β)-2-(hydroxyethyl)-3-<(phenylsulfonyl)amino>-6-oxabicyclo<3.1.0>hexane

There total 7 articles about dl-(1β,2α,3β,5β)-2-(hydroxyethyl)-3-<(phenylsulfonyl)amino>-6-oxabicyclo<3.1.0>hexane 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: 43.4%

dl-trans-2-<2-<(phenylsulfonyl)amino>cyclopent-4-enyl>ethanol (113007-91-3) → dl-(1β,2α,3β,5β)-2-(hydroxyethyl)-3-<(phenylsulfonyl)amino>-6-oxabicyclo<3.1.0>hexane (113084-34-7) + dl-(1α,2α,3β,5α)-2-(hydroxyethyl)-3-<(phenylsulfonyl)amino>-6-oxabicyclo<3.1.0>hexane (113084-33-6)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 15h;

DOI:10.1021/jm00163a038

Reference yield:

1-hydroxy-2-(2-hydroxyethyl)cyclopent-3-ene (49826-08-6,54483-54-4,54483-55-5,75331-67-8) → dl-(1β,2α,3β,5β)-2-(hydroxyethyl)-3-<(phenylsulfonyl)amino>-6-oxabicyclo<3.1.0>hexane (113084-34-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 96 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 h / Ambient temperature

2: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3: NaN₃ / dimethylformamide / 5 h / 75 °C

4: 1.) Ph₃P, 2.) H₂O / 1.) RT, 15 h, 2.) a.) 45 deg C, 2 h, b.) reflux, 1 h

5: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

6: 99 percent / 1 N aq. HCl / tetrahydrofuran; methanol / 2 h / 45 °C

7: 22.6 percent / 80percent 3-chloroperbenzoic acid / CH₂Cl₂ / 15 h / 0 °C

With hydrogenchloride; dmap; sodium azide; water; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00163a038

Reference yield:

dl-trans-2-(2-aminocyclopent-4-enyl)ethanol triphenylmethyl ether (113007-89-9) → dl-(1β,2α,3β,5β)-2-(hydroxyethyl)-3-<(phenylsulfonyl)amino>-6-oxabicyclo<3.1.0>hexane (113084-34-7)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2: 99 percent / 1 N aq. HCl / tetrahydrofuran; methanol / 2 h / 45 °C

3: 22.6 percent / 80percent 3-chloroperbenzoic acid / CH₂Cl₂ / 15 h / 0 °C

With hydrogenchloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm00163a038

upstream raw materials:

dl-trans-2-<2-<(phenylsulfonyl)amino>cyclopent-4-enyl>ethanol

1-hydroxy-2-(2-hydroxyethyl)cyclopent-3-ene

dl-trans-2-(2-aminocyclopent-4-enyl)ethanol triphenylmethyl ether

dl-cis-2-(2-hydroxycyclopent-4-enyl)ethanol triphenylmethyl ether

Downstream raw materials:

dl-(1β,2α,3β,5β)-7-<3-<(phenylsulfonyl)amino>-6-oxabicyclo<3.1.0>hex-2-yl>-5(Z)-heptenoic acid

dl-(1α,2α,3β,5α)-7-<3-<(phenylsulfonyl)amino>-6-thiabicyclo<3.1.0>hex-2-yl>-5(Z)-heptenoic acid

dl-methyl (1β,2α,3β,5β)-7-<3-<(phenylsulfonyl)amino>-6-oxabicyclo<3.1.0>hex-2-yl>-5(Z)-heptenoate

dl-methyl (1α,2α,3β,5α)-7-<3-<(phenylsulfonyl)amino>-6-thiabicyclo<3.1.0>hex-2-yl>-5(Z)-heptenoate