allyl (Z,4R,5S,6R)-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenoate

Base Information

Chemical Name:allyl (Z,4R,5S,6R)-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenoate
CAS No.:862888-55-9
Molecular Formula:C₄₅H₅₅NO₈Si
Molecular Weight:766.019
Hs Code.:

Synonyms:allyl (Z,4R,5S,6R)-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenoate

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Chemical Property of allyl (Z,4R,5S,6R)-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenoate

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Technology Process of allyl (Z,4R,5S,6R)-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenoate

There total 4 articles about allyl (Z,4R,5S,6R)-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenoate 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: 85.1%

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

: 107-18-6
allyl alcohol

: 862888-55-9
allyl (Z,4R,5S,6R)-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenoate

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 19.5h;
DOI:10.1248/cpb.53.529

Reference yield:

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

: 862888-55-9
allyl (Z,4R,5S,6R)-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenoate

Guidance literature:: Multi-step reaction with 3 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 / 19.5 h / 20 °C

With sodium hydroxide; benzotriazol-1-ol; 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

Reference yield:

: 78009-77-5
2,3,5-tri-O-benzyl-4-O-(tert-butyldimethylsilyl)-aldehydo-D-arabinose

: 862888-55-9
allyl (Z,4R,5S,6R)-2-benzyloxycarbonylamino-6-tert-butyldimethylsiloxy-4,5,7-tribenzyloxy-2-heptenoate

Guidance literature:: Multi-step reaction with 3 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 / 19.5 h / 20 °C

With sodium hydroxide; benzotriazol-1-ol; 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