(1aR,8R,9aR)-7-Benzyloxy-5-benzyloxymethoxymethyl-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-oxo-1-(toluene-4-sulfonyl)-1,1a,2,8,9,9a-hexahydro-1,3-diaza-benzo[a]cyclopropa[e]cyclooctene-3-carboxylic acid allyl ester

Base Information

Chemical Name:(1aR,8R,9aR)-7-Benzyloxy-5-benzyloxymethoxymethyl-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-oxo-1-(toluene-4-sulfonyl)-1,1a,2,8,9,9a-hexahydro-1,3-diaza-benzo[a]cyclopropa[e]cyclooctene-3-carboxylic acid allyl ester
CAS No.:194042-00-7
Molecular Formula:C₅₅H₅₈N₂O₉SSi
Molecular Weight:951.225
Hs Code.:

(1aR,8R,9aR)-7-Benzyloxy-5-benzyloxymethoxymethyl-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-oxo-1-(toluene-4-sulfonyl)-1,1a,2,8,9,9a-hexahydro-1,3-diaza-benzo[a]cyclopropa[e]cyclooctene-3-carboxylic acid allyl ester

Synonyms:(1aR,8R,9aR)-7-Benzyloxy-5-benzyloxymethoxymethyl-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-oxo-1-(toluene-4-sulfonyl)-1,1a,2,8,9,9a-hexahydro-1,3-diaza-benzo[a]cyclopropa[e]cyclooctene-3-carboxylic acid allyl ester

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Chemical Property of (1aR,8R,9aR)-7-Benzyloxy-5-benzyloxymethoxymethyl-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-oxo-1-(toluene-4-sulfonyl)-1,1a,2,8,9,9a-hexahydro-1,3-diaza-benzo[a]cyclopropa[e]cyclooctene-3-carboxylic acid allyl ester

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Technology Process of (1aR,8R,9aR)-7-Benzyloxy-5-benzyloxymethoxymethyl-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-oxo-1-(toluene-4-sulfonyl)-1,1a,2,8,9,9a-hexahydro-1,3-diaza-benzo[a]cyclopropa[e]cyclooctene-3-carboxylic acid allyl ester

There total 11 articles about (1aR,8R,9aR)-7-Benzyloxy-5-benzyloxymethoxymethyl-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-oxo-1-(toluene-4-sulfonyl)-1,1a,2,8,9,9a-hexahydro-1,3-diaza-benzo[a]cyclopropa[e]cyclooctene-3-carboxylic acid allyl 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%

: 194041-99-1
(1aR,8R,9R,9aR)-7-Benzyloxy-5-benzyloxymethoxymethyl-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-hydroxy-1-(toluene-4-sulfonyl)-1,1a,2,8,9,9a-hexahydro-1,3-diaza-benzo[a]cyclopropa[e]cyclooctene-3-carboxylic acid allyl ester

: 194042-00-7
(1aR,8R,9aR)-7-Benzyloxy-5-benzyloxymethoxymethyl-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-oxo-1-(toluene-4-sulfonyl)-1,1a,2,8,9,9a-hexahydro-1,3-diaza-benzo[a]cyclopropa[e]cyclooctene-3-carboxylic acid allyl ester

Guidance literature:: With Dess-Martin periodane; In dichloromethane; for 1h; Ambient temperature;
DOI:10.1016/S0040-4020(97)00652-2

Reference yield:

: 98-59-9
p-toluenesulfonyl chloride

: 194042-00-7
(1aR,8R,9aR)-7-Benzyloxy-5-benzyloxymethoxymethyl-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-oxo-1-(toluene-4-sulfonyl)-1,1a,2,8,9,9a-hexahydro-1,3-diaza-benzo[a]cyclopropa[e]cyclooctene-3-carboxylic acid allyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: Et₃N / dimethylformamide / 4 h / Ambient temperature

2: 92 percent / Et₃N / CH₂Cl₂ / 3 h / Ambient temperature

3: 94 percent / NaH, imidazole / paraffin; tetrahydrofuran / Heating

4: 98 percent / (HF)n*Py / 0.67 h / -10 °C

5: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / Ambient temperature

6: 1.) LiN(TMS)2, 2.) NaBH₄ / 1.) THF, -78 deg C -> -5 deg C, 3 h, 2.) H₂O, 0 deg C, 20 min

7: 80 percent / Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

8: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / Ambient temperature

With 1H-imidazole; dmap; sodium tetrahydroborate; (HF)n*Py; sodium hydride; Dess-Martin periodane; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; paraffin;
DOI:10.1016/S0040-4020(97)00652-2

Reference yield:

: 177957-70-9
{3-Benzyloxy-5-benzyloxymethoxymethyl-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-carbamic acid allyl ester

: 194042-00-7
(1aR,8R,9aR)-7-Benzyloxy-5-benzyloxymethoxymethyl-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-oxo-1-(toluene-4-sulfonyl)-1,1a,2,8,9,9a-hexahydro-1,3-diaza-benzo[a]cyclopropa[e]cyclooctene-3-carboxylic acid allyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 99 percent / NaH / paraffin; tetrahydrofuran / 1.) -78 deg C -> room temperature, 4 h, 2.) room temperature, 2 h

2: 21.2 g / Zn, AcOH / tetrahydrofuran; H₂O / 1 h / Ambient temperature

3: Et₃N / dimethylformamide / 4 h / Ambient temperature

4: 92 percent / Et₃N / CH₂Cl₂ / 3 h / Ambient temperature

5: 94 percent / NaH, imidazole / paraffin; tetrahydrofuran / Heating

6: 98 percent / (HF)n*Py / 0.67 h / -10 °C

7: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / Ambient temperature

8: 1.) LiN(TMS)2, 2.) NaBH₄ / 1.) THF, -78 deg C -> -5 deg C, 3 h, 2.) H₂O, 0 deg C, 20 min

9: 80 percent / Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

10: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / Ambient temperature

With 1H-imidazole; dmap; sodium tetrahydroborate; (HF)n*Py; sodium hydride; Dess-Martin periodane; acetic acid; triethylamine; lithium hexamethyldisilazane; zinc; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; paraffin;
DOI:10.1016/S0040-4020(97)00652-2