(1S,2S,4S,5R)-1-[(benzyloxy)methyl]-2-hydroxy-4-N-acetylaminobicyclo[3.1.0]hexane

Base Information

Chemical Name:(1S,2S,4S,5R)-1-[(benzyloxy)methyl]-2-hydroxy-4-N-acetylaminobicyclo[3.1.0]hexane
CAS No.:188295-96-7
Molecular Formula:C₁₆H₂₁NO₃
Molecular Weight:275.348
Hs Code.:

Synonyms:(1S,2S,4S,5R)-1-[(benzyloxy)methyl]-2-hydroxy-4-N-acetylaminobicyclo[3.1.0]hexane

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Chemical Property of (1S,2S,4S,5R)-1-[(benzyloxy)methyl]-2-hydroxy-4-N-acetylaminobicyclo[3.1.0]hexane

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Technology Process of (1S,2S,4S,5R)-1-[(benzyloxy)methyl]-2-hydroxy-4-N-acetylaminobicyclo[3.1.0]hexane

There total 3 articles about (1S,2S,4S,5R)-1-[(benzyloxy)methyl]-2-hydroxy-4-N-acetylaminobicyclo[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: 50.0%

: 75-11-6
diiodomethane

: 188295-94-5
(1S,4S)-2-[(benzyloxy)methyl]-4-N-acetylaminocyclopent-2-enol

: 188295-96-7
(1S,2S,4S,5R)-1-[(benzyloxy)methyl]-2-hydroxy-4-N-acetylaminobicyclo[3.1.0]hexane

Guidance literature:: With diethylzinc; In hexane; dichloromethane; room temp., 10 min, then 0 deg C -> room temp., overnight;
DOI:10.1016/S0040-4039(96)02425-2

Reference yield:

: (1S,4S)-3-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-cyclopent-2-enylamine

: 188295-96-7
(1S,2S,4S,5R)-1-[(benzyloxy)methyl]-2-hydroxy-4-N-acetylaminobicyclo[3.1.0]hexane

Guidance literature:: Multi-step reaction with 3 steps

1: 82 percent / Et₃N / tetrahydrofuran / 0 deg C -> room temp., then room temp., 45 min

2: 100 percent / TBAF / tetrahydrofuran / Ambient temperature

3: 50 percent / Et₂Zn / CH₂Cl₂; hexane / room temp., 10 min, then 0 deg C -> room temp., overnight

With tetrabutyl ammonium fluoride; diethylzinc; triethylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1016/S0040-4039(96)02425-2

Reference yield:

: 188295-92-3
(1S,4S)-1-O-(tert-butyldiphenylsilyl)-2-[(benzloxy)methyl]-4-N-acetylaminocyclopent-2-enol

: 188295-96-7
(1S,2S,4S,5R)-1-[(benzyloxy)methyl]-2-hydroxy-4-N-acetylaminobicyclo[3.1.0]hexane

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / TBAF / tetrahydrofuran / Ambient temperature

2: 50 percent / Et₂Zn / CH₂Cl₂; hexane / room temp., 10 min, then 0 deg C -> room temp., overnight

With tetrabutyl ammonium fluoride; diethylzinc; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1016/S0040-4039(96)02425-2