Acetic acid (1R,2S,3S,4R,5R)-2-acetoxy-3-(2-chloro-acetylamino)-4-(3-oxo-3-phenyl-propyl)-5-triisopropylsilanyloxy-cyclopentyl ester

Base Information

Chemical Name:Acetic acid (1R,2S,3S,4R,5R)-2-acetoxy-3-(2-chloro-acetylamino)-4-(3-oxo-3-phenyl-propyl)-5-triisopropylsilanyloxy-cyclopentyl ester
CAS No.:172909-51-2
Molecular Formula:C₂₉H₄₄ClNO₇Si
Molecular Weight:582.209
Hs Code.:

Synonyms:Acetic acid (1R,2S,3S,4R,5R)-2-acetoxy-3-(2-chloro-acetylamino)-4-(3-oxo-3-phenyl-propyl)-5-triisopropylsilanyloxy-cyclopentyl ester

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Chemical Property of Acetic acid (1R,2S,3S,4R,5R)-2-acetoxy-3-(2-chloro-acetylamino)-4-(3-oxo-3-phenyl-propyl)-5-triisopropylsilanyloxy-cyclopentyl ester

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Technology Process of Acetic acid (1R,2S,3S,4R,5R)-2-acetoxy-3-(2-chloro-acetylamino)-4-(3-oxo-3-phenyl-propyl)-5-triisopropylsilanyloxy-cyclopentyl ester

There total 8 articles about Acetic acid (1R,2S,3S,4R,5R)-2-acetoxy-3-(2-chloro-acetylamino)-4-(3-oxo-3-phenyl-propyl)-5-triisopropylsilanyloxy-cyclopentyl 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: 60.0%

: 100-58-3
phenylmagnesium bromide

: 172909-50-1
Acetic acid (1R,2S,3S,4R,5R)-2-acetoxy-3-(2-chloro-acetylamino)-4-(3-oxo-propyl)-5-triisopropylsilanyloxy-cyclopentyl ester

: 172909-51-2
Acetic acid (1R,2S,3S,4R,5R)-2-acetoxy-3-(2-chloro-acetylamino)-4-(3-oxo-3-phenyl-propyl)-5-triisopropylsilanyloxy-cyclopentyl ester

Guidance literature:: With lithium bromide; In tetrahydrofuran;
DOI:10.1021/ja00152a026

Reference yield:

: (3aS,4R,5R,6R,6aS)-4-Allyl-2-chloromethyl-5-triisopropylsilanyloxy-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-6-ol

: 172909-51-2
Acetic acid (1R,2S,3S,4R,5R)-2-acetoxy-3-(2-chloro-acetylamino)-4-(3-oxo-3-phenyl-propyl)-5-triisopropylsilanyloxy-cyclopentyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) PPTS, 2.) DMAP / 1.) H₂O, MeCN,

2: 83 percent / Chx₂BH, H₂O₂ / diethyl ether

3: 83 percent / (COCl)2, DMSO

4: 60 percent / LiBr / tetrahydrofuran

With dmap; oxalyl dichloride; bis(cyclohexanyl)borane; dihydrogen peroxide; pyridinium p-toluenesulfonate; dimethyl sulfoxide; lithium bromide; In tetrahydrofuran; diethyl ether;
DOI:10.1021/ja00152a026

Reference yield:

: 172909-44-3
(1aR,5aR,8S,8aR)-4-Trichloromethyl-8-triisopropylsilanyloxy-1a,2,5a,8-tetrahydro-1H-3-oxa-5-aza-cyclopropa[d]azulene

: 172909-51-2
Acetic acid (1R,2S,3S,4R,5R)-2-acetoxy-3-(2-chloro-acetylamino)-4-(3-oxo-3-phenyl-propyl)-5-triisopropylsilanyloxy-cyclopentyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 80 percent / Li₂NiBr₄ / tetrahydrofuran

2: 65 percent / dimethyldioxirane / acetone

3: 87 percent / BF₃*Et₂O / toluene

4: 75 percent / Bu₃SnH, Et₃B, NaBH₄ / ethanol

5: 1.) PPTS, 2.) DMAP / 1.) H₂O, MeCN,

6: 83 percent / Chx₂BH, H₂O₂ / diethyl ether

7: 83 percent / (COCl)2, DMSO

8: 60 percent / LiBr / tetrahydrofuran

With dmap; sodium tetrahydroborate; oxalyl dichloride; triethyl borane; dilithium tetrabromonickelate(II); boron trifluoride diethyl etherate; bis(cyclohexanyl)borane; dihydrogen peroxide; tri-n-butyl-tin hydride; 3,3-dimethyldioxirane; pyridinium p-toluenesulfonate; dimethyl sulfoxide; lithium bromide; In tetrahydrofuran; diethyl ether; ethanol; acetone; toluene;
DOI:10.1021/ja00152a026