Methanesulfonic acid (1S,2S,3R)-2-(4-benzyloxycarbonylamino-phenyl)-3-methanesulfonyloxymethyl-cyclopropylmethyl ester

Base Information

• Chemical Name: Methanesulfonic acid (1S,2S,3R)-2-(4-benzyloxycarbonylamino-phenyl)-3-methanesulfonyloxymethyl-cyclopropylmethyl ester
• CAS No.: 881012-64-2
• Molecular Formula: C₂₁H₂₅NO₈S₂
• Molecular Weight: 483.563
• Mol file: 881012-64-2.mol

Synonyms:Methanesulfonic acid (1S,2S,3R)-2-(4-benzyloxycarbonylamino-phenyl)-3-methanesulfonyloxymethyl-cyclopropylmethyl ester

Chemical Property of Methanesulfonic acid (1S,2S,3R)-2-(4-benzyloxycarbonylamino-phenyl)-3-methanesulfonyloxymethyl-cyclopropylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid (1S,2S,3R)-2-(4-benzyloxycarbonylamino-phenyl)-3-methanesulfonyloxymethyl-cyclopropylmethyl ester

There total 7 articles about Methanesulfonic acid (1S,2S,3R)-2-(4-benzyloxycarbonylamino-phenyl)-3-methanesulfonyloxymethyl-cyclopropylmethyl 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:

[4-((1S,2R,3S)-2,3-Bis-hydroxymethyl-cyclopropyl)-phenyl]-carbamic acid benzyl ester (777089-61-9) + Methanesulfonic anhydride (7143-01-3) → Methanesulfonic acid (1S,2S,3R)-2-(4-benzyloxycarbonylamino-phenyl)-3-methanesulfonyloxymethyl-cyclopropylmethyl ester (881012-64-2)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/ol050730h

Reference yield:

benzyl 4-[(1E)-3-hydroxyprop-1-enyl]phenylcarbamate (777089-58-4) → Methanesulfonic acid (1S,2S,3R)-2-(4-benzyloxycarbonylamino-phenyl)-3-methanesulfonyloxymethyl-cyclopropylmethyl ester (881012-64-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Me₂CH=C(Cl)NMe₂ / CH₂Cl₂ / 0.67 h / 23 °C

1.2: N,N-dimethylaniline; Et₃N / CH₂Cl₂ / 0 - 20 °C

2.1: bis(N-t-butylsalicylaldiminato)copper(II) / 1,2-dichloro-ethane; toluene / Heating

3.1: LiBH₄ / tetrahydrofuran / 0 - 20 °C

4.1: Et₃N / CH₂Cl₂ / 0 - 20 °C

With lithium borohydride; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; triethylamine; bis(N-tert-butylsalicylaldiminato)copper(II); In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; toluene;

DOI:10.1021/ol050730h

Reference yield:

methyl (2E)-3-(4-{[(benzyloxy)carbonyl]amino}phenyl)acrylate (777089-57-3) → Methanesulfonic acid (1S,2S,3R)-2-(4-benzyloxycarbonylamino-phenyl)-3-methanesulfonyloxymethyl-cyclopropylmethyl ester (881012-64-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 52 percent / LiAlH₄ / tetrahydrofuran / -78 - -20 °C

2.1: Me₂CH=C(Cl)NMe₂ / CH₂Cl₂ / 0.67 h / 23 °C

2.2: N,N-dimethylaniline; Et₃N / CH₂Cl₂ / 0 - 20 °C

3.1: bis(N-t-butylsalicylaldiminato)copper(II) / 1,2-dichloro-ethane; toluene / Heating

4.1: LiBH₄ / tetrahydrofuran / 0 - 20 °C

5.1: Et₃N / CH₂Cl₂ / 0 - 20 °C

With lithium aluminium tetrahydride; lithium borohydride; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; triethylamine; bis(N-tert-butylsalicylaldiminato)copper(II); In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; toluene;

DOI:10.1021/ol050730h

upstream raw materials:

[4-((1S,2R,3S)-2,3-Bis-hydroxymethyl-cyclopropyl)-phenyl]-carbamic acid benzyl ester

Methanesulfonic anhydride

methyl (2E)-3-(4-{[(benzyloxy)carbonyl]amino}phenyl)acrylate

benzyl 4-[(1E)-3-hydroxyprop-1-enyl]phenylcarbamate

Downstream raw materials:

{4-[(1S,5R,6S)-3-(4-Methoxy-benzyl)-3-aza-bicyclo[3.1.0]hex-6-yl]-phenyl}-carbamic acid benzyl ester

[(1S,5R,6S)-4-(3-Thia-bicyclo[3.1.0]hex-6-yl)-phenyl]-carbamic acid benzyl ester

Refernces

• 1、 Renslo, Adam R.,Gao, Hongwu,Jaishankar, Priyadarshini,Venkatachalam, Revathy,Gordeev, Mikhail F.. "Synthesis of aza-, oxa-, and thiabicyclo[3.1.0]hexane heterocycles from a common synthetic intermediate". . p. 2627 - 2630. Retrieved 2007/10/03.