(1R,2S,3S,5S)-7,7-(2',2'-dimethyltrimethylenedioxy)-3-(4-nitrobenzylsulfonyloxy)bicyclo[3.3.0]octane-2-carboxylic acid methyl ester

Base Information

Chemical Name:(1R,2S,3S,5S)-7,7-(2',2'-dimethyltrimethylenedioxy)-3-(4-nitrobenzylsulfonyloxy)bicyclo[3.3.0]octane-2-carboxylic acid methyl ester
CAS No.:474434-29-2
Molecular Formula:C₂₁H₂₇NO₉S
Molecular Weight:469.513
Hs Code.:

Synonyms:(1R,2S,3S,5S)-7,7-(2',2'-dimethyltrimethylenedioxy)-3-(4-nitrobenzylsulfonyloxy)bicyclo[3.3.0]octane-2-carboxylic acid methyl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1R,2S,3S,5S)-7,7-(2',2'-dimethyltrimethylenedioxy)-3-(4-nitrobenzylsulfonyloxy)bicyclo[3.3.0]octane-2-carboxylic acid methyl ester

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Technology Process of (1R,2S,3S,5S)-7,7-(2',2'-dimethyltrimethylenedioxy)-3-(4-nitrobenzylsulfonyloxy)bicyclo[3.3.0]octane-2-carboxylic acid methyl ester

There total 1 articles about (1R,2S,3S,5S)-7,7-(2',2'-dimethyltrimethylenedioxy)-3-(4-nitrobenzylsulfonyloxy)bicyclo[3.3.0]octane-2-carboxylic acid methyl 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: 95.0%

: 116949-06-5
C₁₅H₂₄O₅

: 98-74-8
4-Nitrobenzenesulfonyl chloride

: 474434-29-2
(1R,2S,3S,5S)-7,7-(2',2'-dimethyltrimethylenedioxy)-3-(4-nitrobenzylsulfonyloxy)bicyclo[3.3.0]octane-2-carboxylic acid methyl ester

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 3h;
DOI:10.1021/jo025857o DOI:10.1055/s-2002-34378

Reference yield:

: 474434-29-2
(1R,2S,3S,5S)-7,7-(2',2'-dimethyltrimethylenedioxy)-3-(4-nitrobenzylsulfonyloxy)bicyclo[3.3.0]octane-2-carboxylic acid methyl ester

: 496972-56-6
methyl (1S,2R,3aS,5R,6aR)-2-{[(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanoyl]amino}-5-hydroxyoctahydropentalene-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 95 percent / NaN₃ / dimethylformamide / 8 h / 20 °C

2.1: 82 percent / H₂ / 10 percent Pd/C / ethyl acetate / 48 h / 20 °C

3.1: 91 percent / TBTU; NNM / dimethylformamide / 1 h / 22 °C

4.1: aq. TFA; Et₃SiH / 4.5 h / 22 °C

4.2: 72 percent / SiO₂ / ethanol / 1 h / 22 °C

With triethylsilane; sodium azide; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; trifluoroacetic acid; palladium on activated charcoal; In ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1055/s-2002-34378

Reference yield:

: 474434-29-2
(1R,2S,3S,5S)-7,7-(2',2'-dimethyltrimethylenedioxy)-3-(4-nitrobenzylsulfonyloxy)bicyclo[3.3.0]octane-2-carboxylic acid methyl ester

: 496972-55-5
methyl (1S,2R,3aS,6aR)-2-[(2S)-3-(4-tert-butoxyphenyl)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propanoylamino]-5,5-(2',2'-dimethyltrimethylenedioxy)octahydropentalene-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / NaN₃ / dimethylformamide / 8 h / 20 °C

2: 82 percent / H₂ / 10 percent Pd/C / ethyl acetate / 48 h / 20 °C

3: 91 percent / TBTU; NNM / dimethylformamide / 1 h / 22 °C

With sodium azide; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; palladium on activated charcoal; In ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1055/s-2002-34378