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

Base Information

Chemical Name:methyl (Z,4R,5S,6R)-4,5,7-tribenzyloxy-2-benzyloxycarbonylamino-6-hydroxy-2-heptenoate
CAS No.:253680-81-8
Molecular Formula:C₃₇H₃₉NO₈
Molecular Weight:625.719
Hs Code.:

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

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

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

There total 13 articles about methyl (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: 88.0%

: 253680-80-7
methyl (Z,4R,5S,6R)-4,5,7-tribenzyloxy-2-benzyloxycarbonylamino-6-(tert-butyldimethylsilyloxy)-2-heptenoate

: methyl (E,4R,5S,6R)-4,5,7-tribenzyloxy-2-benzyloxycarbonylamino-6-hydroxy-2-heptenoate

: 253680-81-8
methyl (Z,4R,5S,6R)-4,5,7-tribenzyloxy-2-benzyloxycarbonylamino-6-hydroxy-2-heptenoate

Guidance literature:: With pyridine hydrogenfluoride; In tetrahydrofuran; pyridine; at 0 - 20 ℃; for 22.5h;
DOI:10.1016/S0040-4020(99)00753-X

Reference yield: 73.0%

: 253680-82-9
methyl (Z,4R,5S,6R)-4,5,7-tribenzyloxy-2-benzyloxycarbonylamino-6-(tert-butyldiphenylsilyloxy)-2-heptenoate

: methyl (E,4R,5S,6R)-4,5,7-tribenzyloxy-2-benzyloxycarbonylamino-6-hydroxy-2-heptenoate

: 253680-81-8
methyl (Z,4R,5S,6R)-4,5,7-tribenzyloxy-2-benzyloxycarbonylamino-6-hydroxy-2-heptenoate

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 9h;
DOI:10.1016/S0040-4020(99)00753-X

Reference yield:

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

: 253680-81-8
methyl (Z,4R,5S,6R)-4,5,7-tribenzyloxy-2-benzyloxycarbonylamino-6-hydroxy-2-heptenoate

Guidance literature:: Multi-step reaction with 7 steps

1: 96 percent / NaBH₄ / ethanol / 0.67 h / 0 °C

2: 74 percent / DMAP; Et₃N / dimethylformamide / 24 h / 20 °C

3: 76 percent / imidazole / dimethylformamide / 48 h / 20 °C

4: 74 percent / p-TsOH / methanol; CH₂Cl₂ / 5 h / 20 °C

5: PDC / CH₂Cl₂ / 24 h / 20 °C

6: 62 percent / DBU / CH₂Cl₂ / 1.5 h / 20 °C

7: 73 percent / TBAF / tetrahydrofuran / 9 h / 20 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; dipyridinium dichromate; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: Reduction / 2: Condensation / 3: Substitution / 4: Hydrolysis / 5: Oxidation / 6: Horner-Emmons reaction / 7: Substitution;
DOI:10.1016/S0040-4020(99)00753-X