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

Base Information

• Chemical Name: (1S,4S)-1-O-(tert-butyldiphenylsilyl)-2-[(benzloxy)methyl]-4-N-acetylaminocyclopent-2-enol
• CAS No.: 188295-92-3
• Molecular Formula: C₂₁H₃₃NO₃Si
• Molecular Weight: 375.583

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

Chemical Property of (1S,4S)-1-O-(tert-butyldiphenylsilyl)-2-[(benzloxy)methyl]-4-N-acetylaminocyclopent-2-enol

Chemical Property:

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Technology Process of (1S,4S)-1-O-(tert-butyldiphenylsilyl)-2-[(benzloxy)methyl]-4-N-acetylaminocyclopent-2-enol

There total 1 articles about (1S,4S)-1-O-(tert-butyldiphenylsilyl)-2-[(benzloxy)methyl]-4-N-acetylaminocyclopent-2-enol 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: 82.0%

acetic anhydride (108-24-7) + (1S,4S)-3-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-cyclopent-2-enylamine → (1S,4S)-1-O-(tert-butyldiphenylsilyl)-2-[(benzloxy)methyl]-4-N-acetylaminocyclopent-2-enol (188295-92-3)

Guidance literature:

With triethylamine; In tetrahydrofuran; 0 deg C -> room temp., then room temp., 45 min;

DOI:10.1016/S0040-4039(96)02425-2

Reference yield: 100.0%

(1S,4S)-1-O-(tert-butyldiphenylsilyl)-2-[(benzloxy)methyl]-4-N-acetylaminocyclopent-2-enol (188295-92-3) → (1S,4S)-2-[(benzyloxy)methyl]-4-N-acetylaminocyclopent-2-enol (188295-94-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/S0040-4039(96)02425-2

Reference yield:

(1S,4S)-1-O-(tert-butyldiphenylsilyl)-2-[(benzloxy)methyl]-4-N-acetylaminocyclopent-2-enol (188295-92-3) → (1S,2S,4S,5R)-1-[(benzyloxy)methyl]-2-hydroxy-4-N-acetylaminobicyclo[3.1.0]hexane (188295-96-7)

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

upstream raw materials:

acetic anhydride

Downstream raw materials:

N-Acetyl-N-[(1S,4S)-3-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-cyclopent-2-enyl]-benzamide

(1S,4S)-2-[(benzyloxy)methyl]-4-N-acetylaminocyclopent-2-enol

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

N-Acetyl-N-((1S,2S,4S,5R)-5-benzyloxymethyl-4-hydroxy-bicyclo[3.1.0]hex-2-yl)-benzamide

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