(1S,2S,3S,4R,5R)-2-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-[1,3]dioxan-2-yl-4,5-bis-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-cyclopentanecarboxylic acid

Base Information

Chemical Name:(1S,2S,3S,4R,5R)-2-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-[1,3]dioxan-2-yl-4,5-bis-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-cyclopentanecarboxylic acid
CAS No.:302908-71-0
Molecular Formula:C₄₃H₄₉N₃O₁₁Si
Molecular Weight:811.961
Hs Code.:

(1S,2S,3S,4R,5R)-2-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-[1,3]dioxan-2-yl-4,5-bis-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-cyclopentanecarboxylic acid

Synonyms:(1S,2S,3S,4R,5R)-2-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-[1,3]dioxan-2-yl-4,5-bis-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-cyclopentanecarboxylic acid

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Chemical Property of (1S,2S,3S,4R,5R)-2-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-[1,3]dioxan-2-yl-4,5-bis-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-cyclopentanecarboxylic acid

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Technology Process of (1S,2S,3S,4R,5R)-2-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-[1,3]dioxan-2-yl-4,5-bis-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-cyclopentanecarboxylic acid

There total 3 articles about (1S,2S,3S,4R,5R)-2-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-[1,3]dioxan-2-yl-4,5-bis-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-cyclopentanecarboxylic acid 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: 100.0%

: 302908-70-9
[(1R,2S,3R,4R,5S)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-[1,3]dioxan-2-yl-3,4-bis-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-5-formyl-cyclopentyl]-carbamic acid benzyl ester

: 302908-71-0
(1S,2S,3S,4R,5R)-2-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-[1,3]dioxan-2-yl-4,5-bis-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-cyclopentanecarboxylic acid

Guidance literature:: With potassium permanganate; In tert-butyl alcohol; at 23 ℃; for 0.75h; pH=7;
DOI:10.1021/ja0019575

Reference yield:

: 302908-69-6
[(2S,3R,4R,5S)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3,4-bis-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2,5-diformyl-cyclopentyl]-carbamic acid benzyl ester

: 302908-71-0
(1S,2S,3S,4R,5R)-2-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-[1,3]dioxan-2-yl-4,5-bis-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-cyclopentanecarboxylic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 59 percent / PPTS / diethyl ether / 1.5 h

2: 100 percent / aq. KMnO₄ / 2-methyl-propan-2-ol / 0.75 h / 23 °C / pH 7

With potassium permanganate; pyridinium p-toluenesulfonate; In diethyl ether; tert-butyl alcohol; 1: acetalization / 2: Masamune's oxidation;
DOI:10.1021/ja0019575

Reference yield:

: [(1S,2S,3R,4R,5R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3,4-bis-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2,5-diformyl-cyclopentyl]-carbamic acid benzyl ester

: 302908-71-0
(1S,2S,3S,4R,5R)-2-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-[1,3]dioxan-2-yl-4,5-bis-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-cyclopentanecarboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 0.410 g / K₂CO₃ / CH₂Cl₂ / 2 h

2: 59 percent / PPTS / diethyl ether / 1.5 h

3: 100 percent / aq. KMnO₄ / 2-methyl-propan-2-ol / 0.75 h / 23 °C / pH 7

With potassium permanganate; pyridinium p-toluenesulfonate; potassium carbonate; In diethyl ether; dichloromethane; tert-butyl alcohol; 1: epimerization / 2: acetalization / 3: Masamune's oxidation;
DOI:10.1021/ja0019575