(Z,4R,5S,6R)-N-2'-oxopropyl-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenamide

Base Information

Chemical Name:(Z,4R,5S,6R)-N-2'-oxopropyl-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenamide
CAS No.:862888-53-7
Molecular Formula:C₄₅H₅₆N₂O₈Si
Molecular Weight:781.034
Hs Code.:

Synonyms:(Z,4R,5S,6R)-N-2'-oxopropyl-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenamide

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Chemical Property of (Z,4R,5S,6R)-N-2'-oxopropyl-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenamide

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Technology Process of (Z,4R,5S,6R)-N-2'-oxopropyl-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenamide

There total 5 articles about (Z,4R,5S,6R)-N-2'-oxopropyl-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenamide 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: 95.1%

: 862888-57-1
(Z,4R,5S,6R)-N-2'-hydroxypropyl-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenamide

: 862888-53-7
(Z,4R,5S,6R)-N-2'-oxopropyl-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenamide

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1248/cpb.53.529

Reference yield:

: 862888-52-6
(Z,4R,5S,6R)-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenoic acid

: 862888-53-7
(Z,4R,5S,6R)-N-2'-oxopropyl-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenamide

Guidance literature:: Multi-step reaction with 2 steps

1: 85.1 percent / 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride; 1-hydroxybenzotriazole; N-ethyldiisopropylamine / CH₂Cl₂ / 23.5 h / 20 °C

2: 95.1 percent / Dess-Martin reagent / CH₂Cl₂ / 1 h / 20 °C

With benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1248/cpb.53.529

Reference yield:

: 100945-15-1,88568-95-0
N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester

: 862888-53-7
(Z,4R,5S,6R)-N-2'-oxopropyl-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenamide

Guidance literature:: Multi-step reaction with 4 steps

1: 67.3 percent / DBU / CH₂Cl₂ / 24 h / 20 °C

2: 100 percent / aq. NaOH / dioxane / 19.5 h / 20 °C

3: 85.1 percent / 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride; 1-hydroxybenzotriazole; N-ethyldiisopropylamine / CH₂Cl₂ / 23.5 h / 20 °C

4: 95.1 percent / Dess-Martin reagent / CH₂Cl₂ / 1 h / 20 °C

With sodium hydroxide; benzotriazol-1-ol; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; dichloromethane; 1: Horner-Emmons reaction;
DOI:10.1248/cpb.53.529