(1R,2S,3S,4S)-1-O-benzyl-4-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidenecyclopentane-1,2,3,4-tetrol

Base Information

Chemical Name:(1R,2S,3S,4S)-1-O-benzyl-4-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidenecyclopentane-1,2,3,4-tetrol
CAS No.:174149-59-8
Molecular Formula:C₂₁H₃₄O₄Si
Molecular Weight:378.584
Hs Code.:

Synonyms:(1R,2S,3S,4S)-1-O-benzyl-4-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidenecyclopentane-1,2,3,4-tetrol

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Chemical Property of (1R,2S,3S,4S)-1-O-benzyl-4-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidenecyclopentane-1,2,3,4-tetrol

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Technology Process of (1R,2S,3S,4S)-1-O-benzyl-4-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidenecyclopentane-1,2,3,4-tetrol

There total 4 articles about (1R,2S,3S,4S)-1-O-benzyl-4-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidenecyclopentane-1,2,3,4-tetrol 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: 95.0%

: 77-76-9
2,2-dimethoxy-propane

: 174149-58-7
(1R,2R,3S,4S)-1-O-benzyl-4-O-(tert-butyldimethylsilyl)cyclopentane-1,2,3,4-tetrol

: 174149-59-8
(1R,2S,3S,4S)-1-O-benzyl-4-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidenecyclopentane-1,2,3,4-tetrol

Guidance literature:: With D-Camphor-10-sulfonic acid; In dichloromethane; for 0.5h; Ambient temperature;
DOI:10.1021/jo951126v

Reference yield:

: 56745-67-6,61305-35-9,61740-33-8,61305-36-0
(4S)-4-tert-butyldimethylsilyloxycyclopent-2-en-1-one

: 174149-59-8
(1R,2S,3S,4S)-1-O-benzyl-4-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidenecyclopentane-1,2,3,4-tetrol

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / DIBALH / benzene; toluene / 2 h / 0 °C

2: 1.) NaH / 1.) THF, room temperature, 30 min, 2.) room temperature, 1 h

3: 1.) AgOAc, I₂, aq. AcOH, 2.) MeONa / 1.) room temperature, 1.5 h; 50 deg C, 4 h, 2.) MeOH, room temperature, 30 min

4: 95 percent / D-camphor-10-dulfonic acid / CH₂Cl₂ / 0.5 h / Ambient temperature

With iodine; sodium methylate; silver(I) acetate; sodium hydride; diisobutylaluminium hydride; D-Camphor-10-sulfonic acid; acetic acid; In dichloromethane; toluene; benzene;
DOI:10.1021/jo951126v

Reference yield:

: 120520-91-4
(1R,4S)-4-(tert-butyldimethylsilyloxy)cyclopent-2-enol

: 174149-59-8
(1R,2S,3S,4S)-1-O-benzyl-4-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidenecyclopentane-1,2,3,4-tetrol

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) NaH / 1.) THF, room temperature, 30 min, 2.) room temperature, 1 h

2: 1.) AgOAc, I₂, aq. AcOH, 2.) MeONa / 1.) room temperature, 1.5 h; 50 deg C, 4 h, 2.) MeOH, room temperature, 30 min

3: 95 percent / D-camphor-10-dulfonic acid / CH₂Cl₂ / 0.5 h / Ambient temperature

With iodine; sodium methylate; silver(I) acetate; sodium hydride; D-Camphor-10-sulfonic acid; acetic acid; In dichloromethane;
DOI:10.1021/jo951126v