(S)-3-Methyl-2-((5S,6S,7S,8S,9S)-5,6,7,8,9-pentakis-benzyloxy-9-(R)-oxiranyl-nonanoylamino)-butyric acid tert-butyl ester

Base Information

Chemical Name:(S)-3-Methyl-2-((5S,6S,7S,8S,9S)-5,6,7,8,9-pentakis-benzyloxy-9-(R)-oxiranyl-nonanoylamino)-butyric acid tert-butyl ester
CAS No.:910630-79-4
Molecular Formula:C₅₅H₆₇NO₉
Molecular Weight:886.138
Hs Code.:

Synonyms:(S)-3-Methyl-2-((5S,6S,7S,8S,9S)-5,6,7,8,9-pentakis-benzyloxy-9-(R)-oxiranyl-nonanoylamino)-butyric acid tert-butyl ester

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Chemical Property of (S)-3-Methyl-2-((5S,6S,7S,8S,9S)-5,6,7,8,9-pentakis-benzyloxy-9-(R)-oxiranyl-nonanoylamino)-butyric acid tert-butyl ester

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Technology Process of (S)-3-Methyl-2-((5S,6S,7S,8S,9S)-5,6,7,8,9-pentakis-benzyloxy-9-(R)-oxiranyl-nonanoylamino)-butyric acid tert-butyl ester

There total 9 articles about (S)-3-Methyl-2-((5S,6S,7S,8S,9S)-5,6,7,8,9-pentakis-benzyloxy-9-(R)-oxiranyl-nonanoylamino)-butyric acid tert-butyl ester 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: 82.0%

: 910630-84-1
(S)-3-Methyl-2-((5S,6S,7S,8S,9S,10R)-5,6,7,8,9-pentakis-benzyloxy-10,11-dihydroxy-undecanoylamino)-butyric acid tert-butyl ester

: 910630-79-4
(S)-3-Methyl-2-((5S,6S,7S,8S,9S)-5,6,7,8,9-pentakis-benzyloxy-9-(R)-oxiranyl-nonanoylamino)-butyric acid tert-butyl ester

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In chloroform; at 60 ℃;
DOI:10.1021/ol061582d

Reference yield:

: 910630-82-9
(Z)-(7S,8R,9S)-7,8,9-Tris-benzyloxy-9-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-non-5-enoic acid

: 910630-79-4
(S)-3-Methyl-2-((5S,6S,7S,8S,9S)-5,6,7,8,9-pentakis-benzyloxy-9-(R)-oxiranyl-nonanoylamino)-butyric acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 92 percent / BOP reagent; Huenig base / dimethylformamide / 4 h / 0 - 20 °C

2: 76 percent / OsO₄; H₂O; NMO / dioxane / 20 °C

3: 63 percent / TfOH / cyclohexane; CH₂Cl₂ / 4 h / 20 °C

4: 87 percent / aq. AcOH / 7 h / 20 °C

5: 82 percent / DEAD; PPh₃ / CHCl₃ / 60 °C

With osmium(VIII) oxide; N-methyl-2-indolinone; trifluorormethanesulfonic acid; water; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; In 1,4-dioxane; dichloromethane; chloroform; cyclohexane; N,N-dimethyl-formamide;
DOI:10.1021/ol061582d

Reference yield:

: 910630-77-2
(S)-3-Methyl-2-[(Z)-(7S,8R,9S)-7,8,9-tris-benzyloxy-9-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-non-5-enoylamino]-butyric acid tert-butyl ester

: 910630-79-4
(S)-3-Methyl-2-((5S,6S,7S,8S,9S)-5,6,7,8,9-pentakis-benzyloxy-9-(R)-oxiranyl-nonanoylamino)-butyric acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 76 percent / OsO₄; H₂O; NMO / dioxane / 20 °C

2: 63 percent / TfOH / cyclohexane; CH₂Cl₂ / 4 h / 20 °C

3: 87 percent / aq. AcOH / 7 h / 20 °C

4: 82 percent / DEAD; PPh₃ / CHCl₃ / 60 °C

With osmium(VIII) oxide; N-methyl-2-indolinone; trifluorormethanesulfonic acid; water; acetic acid; triphenylphosphine; diethylazodicarboxylate; In 1,4-dioxane; dichloromethane; chloroform; cyclohexane;
DOI:10.1021/ol061582d