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

Base Information

Chemical Name:tert-butyl (Z,4R,5S,6R)-4,5,7-tribenzyloxy-2-benzyloxycarbonylamino-6-hydroxy-2-heptenoate
CAS No.:253680-84-1
Molecular Formula:C₄₀H₄₅NO₈
Molecular Weight:667.799
Hs Code.:

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

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

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

There total 8 articles about tert-butyl (Z,4R,5S,6R)-4,5,7-tribenzyloxy-2-benzyloxycarbonylamino-6-hydroxy-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: 34.0%

: 253680-83-0
tert-butyl (Z,4R,5S,6R)-4,5,7-tribenzyloxy-2-benzyloxycarbonylamino-6-(tert-butyldimethylsilyloxy)-2-heptenoate

: tert-butyl (Z,4R,5S,6R)-4,5,7-tribenzyloxy-2-benzyloxycarbonylamino-6-hydroxy-2-heptenoate

: 253680-84-1
tert-butyl (Z,4R,5S,6R)-4,5,7-tribenzyloxy-2-benzyloxycarbonylamino-6-hydroxy-2-heptenoate

Guidance literature:: With pyridine hydrogenfluoride; In tetrahydrofuran; pyridine; at 0 ℃; for 25h;
DOI:10.1016/S0040-4020(99)00753-X

Reference yield:

: 160549-10-0
2,3,5-tri-O-benzyl-D-arabinofuranose

: 253680-84-1
tert-butyl (Z,4R,5S,6R)-4,5,7-tribenzyloxy-2-benzyloxycarbonylamino-6-hydroxy-2-heptenoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: CH₂Cl₂ / 1 h / 20 °C

1.2: 2.45 g / BF₃*Et₂O / CH₂Cl₂ / 1 h / -20 °C

2.1: 95 percent / imidazole / dimethylformamide / 2 h / 20 °C

3.1: 1.98 g / Hg(ClO₄)2*3H₂O; CaCO₃; H₂O / tetrahydrofuran / 3 h / 20 °C

4.1: 54 percent / DBU / CH₂Cl₂ / 22 h / 20 °C

5.1: 23 percent / HF*pyridine / tetrahydrofuran; pyridine / 25 h / 0 °C

With 1H-imidazole; mercury(II) perchlorate; water; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; calcium carbonate; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide; 1.1: Substitution / 1.2: Rearrangement / 2.1: Substitution / 3.1: Hydrolysis / 4.1: Horner-Emmons reaction / 5.1: Substitution;
DOI:10.1016/S0040-4020(99)00753-X

Reference yield:

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

: 253680-84-1
tert-butyl (Z,4R,5S,6R)-4,5,7-tribenzyloxy-2-benzyloxycarbonylamino-6-hydroxy-2-heptenoate

Guidance literature:: Multi-step reaction with 4 steps

1: 3.05 g / aq. NaOH / dioxane / 3.8 h / 20 °C

2: 2.26 g / DMAP / 2-methyl-propan-2-ol / 3 h / 20 °C

3: 54 percent / DBU / CH₂Cl₂ / 22 h / 20 °C

4: 23 percent / HF*pyridine / tetrahydrofuran; pyridine / 25 h / 0 °C

With dmap; sodium hydroxide; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; 1,4-dioxane; pyridine; dichloromethane; tert-butyl alcohol; 1: Hydrolysis / 2: Etherification / 3: Horner-Emmons reaction / 4: Substitution;
DOI:10.1016/S0040-4020(99)00753-X