2-[(3R,5S)-3-(tert-butyldiphenylsilyloxymethyl)-5-hydroxy-1-(methoxycarbonyl)-5-(toluene-4-sulfonyloxymethyl)heptyl]-3-(2-hydroxyethyl)indole-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:2-[(3R,5S)-3-(tert-butyldiphenylsilyloxymethyl)-5-hydroxy-1-(methoxycarbonyl)-5-(toluene-4-sulfonyloxymethyl)heptyl]-3-(2-hydroxyethyl)indole-1-carboxylic acid tert-butyl ester
CAS No.:548774-89-6
Molecular Formula:C₄₉H₆₃NO₁₀SSi
Molecular Weight:886.191
Hs Code.:

2-[(3R,5S)-3-(tert-butyldiphenylsilyloxymethyl)-5-hydroxy-1-(methoxycarbonyl)-5-(toluene-4-sulfonyloxymethyl)heptyl]-3-(2-hydroxyethyl)indole-1-carboxylic acid tert-butyl ester

Synonyms:2-[(3R,5S)-3-(tert-butyldiphenylsilyloxymethyl)-5-hydroxy-1-(methoxycarbonyl)-5-(toluene-4-sulfonyloxymethyl)heptyl]-3-(2-hydroxyethyl)indole-1-carboxylic acid tert-butyl ester

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Chemical Property of 2-[(3R,5S)-3-(tert-butyldiphenylsilyloxymethyl)-5-hydroxy-1-(methoxycarbonyl)-5-(toluene-4-sulfonyloxymethyl)heptyl]-3-(2-hydroxyethyl)indole-1-carboxylic acid tert-butyl ester

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Technology Process of 2-[(3R,5S)-3-(tert-butyldiphenylsilyloxymethyl)-5-hydroxy-1-(methoxycarbonyl)-5-(toluene-4-sulfonyloxymethyl)heptyl]-3-(2-hydroxyethyl)indole-1-carboxylic acid tert-butyl ester

There total 1 articles about 2-[(3R,5S)-3-(tert-butyldiphenylsilyloxymethyl)-5-hydroxy-1-(methoxycarbonyl)-5-(toluene-4-sulfonyloxymethyl)heptyl]-3-(2-hydroxyethyl)indole-1-carboxylic acid tert-butyl 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: 84.3%

: (+)-2-[(3R,5S)-3-(tert-butyldiphenylsilyloxymethyl)-5-hydroxy-5-(hydroxymethyl)-1-(methoxycarbonyl)heptyl]-3-(2-hydroxyethyl)indole-1-carboxylic acid tert-butyl ester

: 98-59-9
p-toluenesulfonyl chloride

: 548774-89-6
2-[(3R,5S)-3-(tert-butyldiphenylsilyloxymethyl)-5-hydroxy-1-(methoxycarbonyl)-5-(toluene-4-sulfonyloxymethyl)heptyl]-3-(2-hydroxyethyl)indole-1-carboxylic acid tert-butyl ester

Guidance literature:: With di(n-butyl)tin oxide; triethylamine; In dichloromethane; at 20 ℃; for 15h;
DOI:10.1021/ja0177049

Reference yield: 90.0%

: 548774-89-6
2-[(3R,5S)-3-(tert-butyldiphenylsilyloxymethyl)-5-hydroxy-1-(methoxycarbonyl)-5-(toluene-4-sulfonyloxymethyl)heptyl]-3-(2-hydroxyethyl)indole-1-carboxylic acid tert-butyl ester

: 548774-90-9
2-[(3R)-3-(tert-butyldiphenylsilyloxymethyl)-4-[(S)-2-ethyloxiran-2-yl]-1-(methoxycarbonyl)butyl]-3-(2-hydroxyethyl)indole-1-carboxylic acid tert-butyl ester

Guidance literature:: With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 80 ℃; for 3h;
DOI:10.1021/ja0177049

Reference yield:

: 548774-89-6
2-[(3R,5S)-3-(tert-butyldiphenylsilyloxymethyl)-5-hydroxy-1-(methoxycarbonyl)-5-(toluene-4-sulfonyloxymethyl)heptyl]-3-(2-hydroxyethyl)indole-1-carboxylic acid tert-butyl ester

: 548774-92-1
C₅₃H₆₆N₄O₁₂S

Guidance literature:: Multi-step reaction with 10 steps

1: 90 percent / NaHCO₃ / dimethylformamide / 3 h / 80 °C

2: 88.3 percent / DEAD; Ph₃P / toluene / 0.67 h / 20 °C

3: 81.5 percent / K₂CO₃ / dimethylformamide / 22 h / 90 °C

4: 84.5 percent / TFA / CH₂Cl₂ / 2 h / 20 °C

5: 87.8 percent / Me₂N(CH₂)3NMe₂ / acetonitrile; toluene / 1 h / 20 °C

6: 90.3 percent / pyridine / CH₂Cl₂ / 0.33 h / 20 °C

7: t-BuOCl / CH₂Cl₂ / 0.17 h / 0 °C

8: TFA / CH₂Cl₂ / 1 h / 0 - 20 °C

9: 100 percent / Et₃N; MeOH / 0.67 h / 20 °C

10: 76 percent / HSCH₂CH₂OH; DBU / acetone / 20 °C

With pyridine; methanol; tert-butylhypochlorite; N,N,N'N'-tetramethyl-1,3-propanediamine; sodium hydrogencarbonate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; trifluoroacetic acid; 2-hydroxyethanethiol; diethylazodicarboxylate; In dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 2: Mitsunobu reaction;
DOI:10.1021/ja0177049