methyl (2S,3R,4R)-4-(benzoylamino)-1-[(benzyloxy)carbonyl]-3-{[(tert-butoxy)carbonyl]amino}prolinate

Base Information

Chemical Name:methyl (2S,3R,4R)-4-(benzoylamino)-1-[(benzyloxy)carbonyl]-3-{[(tert-butoxy)carbonyl]amino}prolinate
CAS No.:215719-37-2
Molecular Formula:C₂₆H₃₁N₃O₇
Molecular Weight:497.548
Hs Code.:

Synonyms:methyl (2S,3R,4R)-4-(benzoylamino)-1-[(benzyloxy)carbonyl]-3-{[(tert-butoxy)carbonyl]amino}prolinate

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Chemical Property of methyl (2S,3R,4R)-4-(benzoylamino)-1-[(benzyloxy)carbonyl]-3-{[(tert-butoxy)carbonyl]amino}prolinate

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Technology Process of methyl (2S,3R,4R)-4-(benzoylamino)-1-[(benzyloxy)carbonyl]-3-{[(tert-butoxy)carbonyl]amino}prolinate

There total 11 articles about methyl (2S,3R,4R)-4-(benzoylamino)-1-[(benzyloxy)carbonyl]-3-{[(tert-butoxy)carbonyl]amino}prolinate 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:

: (1S,4S,5S)-6-(2,4-Dimethoxy-benzyl)-4-hydroxy-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

: 215719-37-2
methyl (2S,3R,4R)-4-(benzoylamino)-1-[(benzyloxy)carbonyl]-3-{[(tert-butoxy)carbonyl]amino}prolinate

Guidance literature:: Multi-step reaction with 7 steps

1: 61 percent / PPh₃; DEAD / tetrahydrofuran / 19 h / -30 - 20 °C

2: methylhydrazine / dimethylformamide / 1.5 h / 80 °C

3: 5.0 g / Et₃N / CH₂Cl₂

4: 77 percent / K₂S₂O₈; Na₂HPO₄*2H₂O / H₂O; acetonitrile / 0.92 h / Heating

5: 60 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h

6: H₂O; Na₂CO₃ / tetrahydrofuran

7: 1.26 g / ethyl acetate; diethyl ether

With dmap; disodium hydrogenphosphate; dipotassium peroxodisulfate; water; sodium carbonate; triethylamine; triphenylphosphine; methylhydrazine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1: Mitsunobu reaction / 2: hydrazinolysis / 3: Acylation / 4: Reduction / 5: Acylation / 6: Hydrolysis / 7: Esterification;
DOI:10.1002/(SICI)1522-2675(20000216)83:2<444::AID-HLCA444>3.0.CO;2-R

Reference yield:

: 215719-40-7
(1S,4R,5R)-4-Benzoylamino-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

: 215719-37-2
methyl (2S,3R,4R)-4-(benzoylamino)-1-[(benzyloxy)carbonyl]-3-{[(tert-butoxy)carbonyl]amino}prolinate

Guidance literature:: Multi-step reaction with 3 steps

1: 60 percent / Et₃N, DMAP / CH₂Cl₂

2: Na₂CO₃, H₂O / tetrahydrofuran

3: diethyl ether

With dmap; water; sodium carbonate; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1039/a804412k

Reference yield:

: 215719-36-1
(1S,4R,5R)-4-Benzoylamino-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2,6-dicarboxylic acid 2-benzyl ester 6-tert-butyl ester

: 215719-37-2
methyl (2S,3R,4R)-4-(benzoylamino)-1-[(benzyloxy)carbonyl]-3-{[(tert-butoxy)carbonyl]amino}prolinate

Guidance literature:: Multi-step reaction with 2 steps

1: Na₂CO₃, H₂O / tetrahydrofuran

2: diethyl ether

With water; sodium carbonate; In tetrahydrofuran; diethyl ether;
DOI:10.1039/a804412k