tert-butyl <(1R,2R,3S,4R)-3-endo-(benzyloxy)-5-oxo-7-oxabicyclo<2.2.1>hept-2-exo-yl>carbamate

Base Information

• Chemical Name: tert-butyl <(1R,2R,3S,4R)-3-endo-(benzyloxy)-5-oxo-7-oxabicyclo<2.2.1>hept-2-exo-yl>carbamate
• CAS No.: 126372-06-3
• Molecular Formula: C₁₈H₂₃NO₅
• Molecular Weight: 333.384

Synonyms:tert-butyl <(1R,2R,3S,4R)-3-endo-(benzyloxy)-5-oxo-7-oxabicyclo<2.2.1>hept-2-exo-yl>carbamate

Chemical Property of tert-butyl <(1R,2R,3S,4R)-3-endo-(benzyloxy)-5-oxo-7-oxabicyclo<2.2.1>hept-2-exo-yl>carbamate

Chemical Property:

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Technology Process of tert-butyl <(1R,2R,3S,4R)-3-endo-(benzyloxy)-5-oxo-7-oxabicyclo<2.2.1>hept-2-exo-yl>carbamate

There total 6 articles about tert-butyl <(1R,2R,3S,4R)-3-endo-(benzyloxy)-5-oxo-7-oxabicyclo<2.2.1>hept-2-exo-yl>carbamate 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: 76.0%

(1RS,2SR,4RS,5RS)-(tert-butyl) 6,6-bis-(benzyloxy)-3-aza-8-oxatricyclo<3.2.1.02,4>octane-3-carboxylate (120235-19-0,126372-20-1,132077-51-1) → tert-butyl <(1RS,2RS,3SR,4RS)-3-endo-(benzyloxy)-5-oxo-7-oxabicyclo<2.2.1>hept-2-exo-yl>carbamate (120235-23-6,126372-06-3,126373-96-4)

Guidance literature:

With trifluoroacetic acid; In chloroform; at 20 ℃; for 24h;

DOI:10.1002/hlca.19890720504

Reference yield: 24.0%

(1R,2S,6R,7R)-8,8-Bis-benzyloxy-10-oxa-3,4,5-triaza-tricyclo[5.2.1.02,6]dec-4-ene-3-carboxylic acid tert-butyl ester (120235-11-2,126372-18-7,132077-44-2) → ((2R,3S)-3-tert-Butoxycarbonylamino-2,3-dihydro-furan-2-yl)-acetic acid benzyl ester (120235-28-1) + tert-butyl <(1RS,2RS,3SR,4RS)-3-endo-(benzyloxy)-5-oxo-7-oxabicyclo<2.2.1>hept-2-exo-yl>carbamate (120235-23-6,126372-06-3,126373-96-4) + ((2S,3R)-5-Benzyloxy-3-tert-butoxycarbonylamino-tetrahydro-furan-2-yl)-acetic acid benzyl ester (120235-29-2) + ((1R,2R,3S,4R)-3,5,5-Tris-benzyloxy-7-oxa-bicyclo[2.2.1]hept-2-yl)-carbamic acid tert-butyl ester (120235-27-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; acetic acid; In dichloromethane; at -10 ℃; for 10h;

DOI:10.1016/S0040-4039(00)82156-5

Reference yield:

N-(tert-butyloxycarbonyl) azide (1070-19-5) → tert-butyl <(1RS,2RS,3SR,4RS)-3-endo-(benzyloxy)-5-oxo-7-oxabicyclo<2.2.1>hept-2-exo-yl>carbamate (120235-23-6,126372-06-3,126373-96-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) acetone, 50 deg C, 24 h; 2.) acetone, irradiation, 2 h

2: 76 percent / CF₃COOH / CHCl₃ / 24 h / 20 °C

With trifluoroacetic acid; In chloroform;

DOI:10.1002/hlca.19890720504

upstream raw materials:

(1RS,2SR,4RS,5RS)-(tert-butyl) 6,6-bis-(benzyloxy)-3-aza-8-oxatricyclo<3.2.1.0^2,4>octane-3-carboxylate

(1R,2S,6R,7R)-8,8-Bis-benzyloxy-10-oxa-3,4,5-triaza-tricyclo[5.2.1.0^2,6]dec-4-ene-3-carboxylic acid tert-butyl ester

N-(tert-butyloxycarbonyl) azide

7-oxabicyclo<2.2.1>hept-5-en-2-one dibenzyl acetal

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