(2S,3R,4R,5S)-rac-5-(3-azidopropyl)-2,3-dihydroxy-5-(phenylsulfonyl)-4-<6-vinyl-3,4-(methylenedioxy)phenyl>cyclopentane

Base Information

Chemical Name:(2S,3R,4R,5S)-rac-5-(3-azidopropyl)-2,3-dihydroxy-5-(phenylsulfonyl)-4-<6-vinyl-3,4-(methylenedioxy)phenyl>cyclopentane
CAS No.:105064-23-1
Molecular Formula:C₂₃H₂₅N₃O₆S
Molecular Weight:471.534
Hs Code.:

Synonyms:(2S,3R,4R,5S)-rac-5-(3-azidopropyl)-2,3-dihydroxy-5-(phenylsulfonyl)-4-<6-vinyl-3,4-(methylenedioxy)phenyl>cyclopentane

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Chemical Property of (2S,3R,4R,5S)-rac-5-(3-azidopropyl)-2,3-dihydroxy-5-(phenylsulfonyl)-4-<6-vinyl-3,4-(methylenedioxy)phenyl>cyclopentane

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Technology Process of (2S,3R,4R,5S)-rac-5-(3-azidopropyl)-2,3-dihydroxy-5-(phenylsulfonyl)-4-<6-vinyl-3,4-(methylenedioxy)phenyl>cyclopentane

There total 11 articles about (2S,3R,4R,5S)-rac-5-(3-azidopropyl)-2,3-dihydroxy-5-(phenylsulfonyl)-4-<6-vinyl-3,4-(methylenedioxy)phenyl>cyclopentane 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:

: 105064-22-0
5-[(1R,2S,4S,5R)-2-(3-Azido-propyl)-2-benzenesulfonyl-4,5-diisopropoxy-cyclopentyl]-6-vinyl-benzo[1,3]dioxole

: 105064-23-1
(2S,3R,4R,5S)-rac-5-(3-azidopropyl)-2,3-dihydroxy-5-(phenylsulfonyl)-4-<6-vinyl-3,4-(methylenedioxy)phenyl>cyclopentane

Guidance literature:: With toluene-4-sulfonic acid; In methanol; water; at 25 ℃; for 48h; Yield given;
DOI:10.1021/jo00380a019

Reference yield:

: 120-57-0,30024-74-9
piperonal

: 105064-23-1
(2S,3R,4R,5S)-rac-5-(3-azidopropyl)-2,3-dihydroxy-5-(phenylsulfonyl)-4-<6-vinyl-3,4-(methylenedioxy)phenyl>cyclopentane

Guidance literature:: Multi-step reaction with 4 steps

1: 84 percent / Fe⁽⁰⁾, Br₂ / acetic acid

2: 86 percent / 5N aq. NaOH / benzene / 48 h

3: 1.) t-BuLi, 2.) HMPA / 1.) pentane, ether, -78 deg C, 20 min, 2.) THF, from -78 deg C to 25 deg C

4: p-toluenesulfonic acid / methanol; H₂O / 48 h / 25 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; bromine; tert.-butyl lithium; iron; toluene-4-sulfonic acid; In methanol; water; acetic acid; benzene;
DOI:10.1021/jo00380a019

Reference yield:

: 15930-53-7
6-bromo-3,4-methylenedioxybenzaldehyde

: 105064-23-1
(2S,3R,4R,5S)-rac-5-(3-azidopropyl)-2,3-dihydroxy-5-(phenylsulfonyl)-4-<6-vinyl-3,4-(methylenedioxy)phenyl>cyclopentane

Guidance literature:: Multi-step reaction with 3 steps

1: 86 percent / 5N aq. NaOH / benzene / 48 h

2: 1.) t-BuLi, 2.) HMPA / 1.) pentane, ether, -78 deg C, 20 min, 2.) THF, from -78 deg C to 25 deg C

3: p-toluenesulfonic acid / methanol; H₂O / 48 h / 25 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; tert.-butyl lithium; toluene-4-sulfonic acid; In methanol; water; benzene;
DOI:10.1021/jo00380a019