(1S,2S,5R)-3-Boc-2-[(tert-butyldimethylsilyloxy)methyl]-4-oxo-3-azabicyclo[3.1.0]hexane

Base Information

• Chemical Name: (1S,2S,5R)-3-Boc-2-[(tert-butyldimethylsilyloxy)methyl]-4-oxo-3-azabicyclo[3.1.0]hexane
• CAS No.: 220623-07-4
• Molecular Formula: C17H31NO4Si
• Molecular Weight: 341.523
• Mol file: 220623-07-4.mol

Synonyms:(1S,2S,5R)-3-Boc-2-[(tert-butyldimethylsilyloxy)methyl]-4-oxo-3-azabicyclo[3.1.0]hexane

Chemical Property of (1S,2S,5R)-3-Boc-2-[(tert-butyldimethylsilyloxy)methyl]-4-oxo-3-azabicyclo[3.1.0]hexane

Chemical Property:

• PSA: 55.84000
• LogP: 3.72810

Purity/Quality:

97% ^*data from raw suppliers

(1S,2S,5R)-3-Boc-2-[(tert-butyldimethylsilyloxy)methyl]-4-oxo-3-azabicyclo[3.1.0]hexane 95% ee ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,5R)-3-Boc-2-[(tert-butyldimethylsilyloxy)methyl]-4-oxo-3-azabicyclo[3.1.0]hexane

There total 14 articles about (1S,2S,5R)-3-Boc-2-[(tert-butyldimethylsilyloxy)methyl]-4-oxo-3-azabicyclo[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: 19.0%

(dimethylamino)phenyloxosulfonium methylide (30004-64-9,344752-32-5) + (S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate (81658-27-7) → (1S,2S,5R)-tert-butyl 3-aza-4-oxo-2-<(1,1,2,2-tetramethyl-1-silapropoxy)methyl>bicyclo<3.1.0>hexane-3-carboxylate (220623-07-4) + 2,2'-bis-(tert-butyl-dimethyl-silanyloxymethyl)-5,5'-dioxo-2,5,2',3',4',5'-hexahydro-[2,3']bipyrrolyl-1,1'-dicarboxylic acid di-tert-butyl ester

Guidance literature:

In dimethyl sulfoxide; Ambient temperature;

DOI:10.1021/jo9816109

Reference yield: 14.0%

(S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate (81658-27-7) → (1S,2S,5R)-tert-butyl 3-aza-4-oxo-2-<(1,1,2,2-tetramethyl-1-silapropoxy)methyl>bicyclo<3.1.0>hexane-3-carboxylate (220623-07-4) + 2,2'-bis-(tert-butyl-dimethyl-silanyloxymethyl)-5,5'-dioxo-2,5,2',3',4',5'-hexahydro-[2,3']bipyrrolyl-1,1'-dicarboxylic acid di-tert-butyl ester

Guidance literature:

With PhS⁽¹⁺⁾(O)(NMe₂)-CH₂^(1-); In dimethyl sulfoxide; Ambient temperature;

DOI:10.1021/jo9816109

Reference yield:

(S)-Pyroglutaminol (17342-08-4) → (1S,2S,5R)-tert-butyl 3-aza-4-oxo-2-<(1,1,2,2-tetramethyl-1-silapropoxy)methyl>bicyclo<3.1.0>hexane-3-carboxylate (220623-07-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylamine / dmap / dichloromethane / 24 h

2.1: dmap / acetonitrile / 12 h / 20 °C

3.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium hexamethyldisilazane / tetrahydrofuran / 0.83 h / 0 - 78 °C

3.2: 2 h / -78 °C

4.1: dihydrogen peroxide / tetrahydrofuran; water / 2 h / 0 °C

5.1: diazomethane / palladium diacetate / diethyl ether / 2 h / 0 °C

With diazomethane; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; dihydrogen peroxide; sodium hexamethyldisilazane; triethylamine; dmap; palladium diacetate; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetonitrile;

upstream raw materials:

diazomethane

(S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

(dimethylamino)phenyloxosulfonium methylide

(2S)-2-[(tert-butoxy)carbonylamino]-4-(methoxycarbonyl)butanoic acid

Downstream raw materials:

{(1S,2S,5R)-3-[(2-methyl-5-phenyl-1,3-thiazol-4-yl)carbonyl]-3-azabicyclo[3.1.0]hex-2-yl}methanol

C₁₇H₁₉N₃OS

N-({(1S,2S,5R)-3-[(2-methyl-5-phenyl-1,3-thiazol-4-yl)carbonyl]-3-azabicyclo[3.1.0]hex-2-yl}methyl)-1,3-benzoxazol-2-amine