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Technology Process of (2S,2aS,2bR,4S,5aR,6S)-5a-Benzenesulfonyl-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methoxy-2b-methyl-1-oxo-octahydro-3-oxa-6a-aza-cyclobuta[a]pentalene-6-carboxylic acid benzyl ester

(2S,2aS,2bR,4S,5aR,6S)-5a-Benzenesulfonyl-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methoxy-2b-methyl-1-oxo-octahydro-3-oxa-6a-aza-cyclobuta[a]pentalene-6-carboxylic acid benzyl ester

Base Information
  • Chemical Name:(2S,2aS,2bR,4S,5aR,6S)-5a-Benzenesulfonyl-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methoxy-2b-methyl-1-oxo-octahydro-3-oxa-6a-aza-cyclobuta[a]pentalene-6-carboxylic acid benzyl ester
  • CAS No.:225220-03-1
  • Molecular Formula:C32H43NO8SSi
  • Molecular Weight:629.847
  • Hs Code.:
(2S,2aS,2bR,4S,5aR,6S)-5a-Benzenesulfonyl-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methoxy-2b-methyl-1-oxo-octahydro-3-oxa-6a-aza-cyclobuta[a]pentalene-6-carboxylic acid benzyl ester

Synonyms:(2S,2aS,2bR,4S,5aR,6S)-5a-Benzenesulfonyl-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methoxy-2b-methyl-1-oxo-octahydro-3-oxa-6a-aza-cyclobuta[a]pentalene-6-carboxylic acid benzyl ester

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Chemical Property of (2S,2aS,2bR,4S,5aR,6S)-5a-Benzenesulfonyl-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methoxy-2b-methyl-1-oxo-octahydro-3-oxa-6a-aza-cyclobuta[a]pentalene-6-carboxylic acid benzyl ester
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Technology Process of (2S,2aS,2bR,4S,5aR,6S)-5a-Benzenesulfonyl-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methoxy-2b-methyl-1-oxo-octahydro-3-oxa-6a-aza-cyclobuta[a]pentalene-6-carboxylic acid benzyl ester

There total 14 articles about (2S,2aS,2bR,4S,5aR,6S)-5a-Benzenesulfonyl-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methoxy-2b-methyl-1-oxo-octahydro-3-oxa-6a-aza-cyclobuta[a]pentalene-6-carboxylic acid benzyl 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:

trimethyl-(5-methyl-furan-2-yloxy)-silane
61550-05-8

trimethyl-(5-methyl-furan-2-yloxy)-silane

(2S,2aS,2bR,4S,5aR,6S)-5a-Benzenesulfonyl-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methoxy-2b-methyl-1-oxo-octahydro-3-oxa-6a-aza-cyclobuta[a]pentalene-6-carboxylic acid benzyl ester
225220-03-1

(2S,2aS,2bR,4S,5aR,6S)-5a-Benzenesulfonyl-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methoxy-2b-methyl-1-oxo-octahydro-3-oxa-6a-aza-cyclobuta[a]pentalene-6-carboxylic acid benzyl ester

Guidance literature:
Multi-step reaction with 10 steps
1: 92 percent / ZnCl2 / CH2Cl2; diethyl ether / 28 h / Ambient temperature
2: 1) NaHMDS / 1) THF, -78 deg C, 10 min, 2) THF, 6 h
3: 94 percent / LiHMDS / tetrahydrofuran / 12 h / Ambient temperature
4: 1) NaHMDS / 1) THF, -78 deg C, 30 min, 2) THF, -78 deg C, 30 min
5: 61 percent / m-CPBA / CH2Cl2 / 1 h / Ambient temperature
6: 83 percent / diisopropyl ethyl amine / benzene / 1 h / 0 °C
7: 66 percent / DIBAL-H / tetrahydrofuran / 0.5 h / Ambient temperature
8: 50 percent / DMAP, Et3N / CH2Cl2 / 22 h / Ambient temperature
9: 81 percent / AgOTf / CH2Cl2 / 0.5 h / Ambient temperature
10: 18 mg / m-CPBA / CH2Cl2 / 10 h / Ambient temperature
With dmap; silver trifluoromethanesulfonate; sodium hexamethyldisilazane; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; zinc(II) chloride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;
DOI:10.1016/S0040-4020(98)01152-1

Reference yield:

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one
76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

(2S,2aS,2bR,4S,5aR,6S)-5a-Benzenesulfonyl-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methoxy-2b-methyl-1-oxo-octahydro-3-oxa-6a-aza-cyclobuta[a]pentalene-6-carboxylic acid benzyl ester
225220-03-1

(2S,2aS,2bR,4S,5aR,6S)-5a-Benzenesulfonyl-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methoxy-2b-methyl-1-oxo-octahydro-3-oxa-6a-aza-cyclobuta[a]pentalene-6-carboxylic acid benzyl ester

Guidance literature:
Multi-step reaction with 10 steps
1: 92 percent / ZnCl2 / CH2Cl2; diethyl ether / 28 h / Ambient temperature
2: 1) NaHMDS / 1) THF, -78 deg C, 10 min, 2) THF, 6 h
3: 94 percent / LiHMDS / tetrahydrofuran / 12 h / Ambient temperature
4: 1) NaHMDS / 1) THF, -78 deg C, 30 min, 2) THF, -78 deg C, 30 min
5: 61 percent / m-CPBA / CH2Cl2 / 1 h / Ambient temperature
6: 83 percent / diisopropyl ethyl amine / benzene / 1 h / 0 °C
7: 66 percent / DIBAL-H / tetrahydrofuran / 0.5 h / Ambient temperature
8: 50 percent / DMAP, Et3N / CH2Cl2 / 22 h / Ambient temperature
9: 81 percent / AgOTf / CH2Cl2 / 0.5 h / Ambient temperature
10: 18 mg / m-CPBA / CH2Cl2 / 10 h / Ambient temperature
With dmap; silver trifluoromethanesulfonate; sodium hexamethyldisilazane; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; zinc(II) chloride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;
DOI:10.1016/S0040-4020(98)01152-1

Reference yield:

thiophenol
108-98-5

thiophenol

(2S,2aS,2bR,4S,5aR,6S)-5a-Benzenesulfonyl-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methoxy-2b-methyl-1-oxo-octahydro-3-oxa-6a-aza-cyclobuta[a]pentalene-6-carboxylic acid benzyl ester
225220-03-1

(2S,2aS,2bR,4S,5aR,6S)-5a-Benzenesulfonyl-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methoxy-2b-methyl-1-oxo-octahydro-3-oxa-6a-aza-cyclobuta[a]pentalene-6-carboxylic acid benzyl ester

Guidance literature:
Multi-step reaction with 5 steps
1: 83 percent / diisopropyl ethyl amine / benzene / 1 h / 0 °C
2: 66 percent / DIBAL-H / tetrahydrofuran / 0.5 h / Ambient temperature
3: 50 percent / DMAP, Et3N / CH2Cl2 / 22 h / Ambient temperature
4: 81 percent / AgOTf / CH2Cl2 / 0.5 h / Ambient temperature
5: 18 mg / m-CPBA / CH2Cl2 / 10 h / Ambient temperature
With dmap; silver trifluoromethanesulfonate; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; benzene;
DOI:10.1016/S0040-4020(98)01152-1
upstream raw materials:

(2S,2aS,2bR,5aR,6S)-2-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-methoxy-2b-methyl-1-oxo-5a-phenylsulfanyl-octahydro-3-oxa-6a-aza-cyclobuta[a]pentalene-6-carboxylic acid benzyl ester

trimethyl-(5-methyl-furan-2-yloxy)-silane

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

thiophenol

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