1β-((tert-butyldimethylsilyl)oxy)-4α-(p-toluenesulfonamido)-2,3-epoxy-6α-(benzyloxy)cycloheptane

Base Information

Chemical Name:1β-((tert-butyldimethylsilyl)oxy)-4α-(p-toluenesulfonamido)-2,3-epoxy-6α-(benzyloxy)cycloheptane
CAS No.:132622-36-7
Molecular Formula:C₂₇H₃₉NO₅SSi
Molecular Weight:517.762
Hs Code.:

Synonyms:1β-((tert-butyldimethylsilyl)oxy)-4α-(p-toluenesulfonamido)-2,3-epoxy-6α-(benzyloxy)cycloheptane

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Chemical Property of 1β-((tert-butyldimethylsilyl)oxy)-4α-(p-toluenesulfonamido)-2,3-epoxy-6α-(benzyloxy)cycloheptane

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Technology Process of 1β-((tert-butyldimethylsilyl)oxy)-4α-(p-toluenesulfonamido)-2,3-epoxy-6α-(benzyloxy)cycloheptane

There total 7 articles about 1β-((tert-butyldimethylsilyl)oxy)-4α-(p-toluenesulfonamido)-2,3-epoxy-6α-(benzyloxy)cycloheptane 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: 96.0%

: 132622-35-6
1β-((tert-butyldimethylsilyl)oxy)-4α-(p-toluenesulfonamido)-6α-(benzyloxy)-2-cycloheptene

: 132622-36-7
1β-((tert-butyldimethylsilyl)oxy)-4α-(p-toluenesulfonamido)-2,3-epoxy-6α-(benzyloxy)cycloheptane

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In chloroform; 1) 0 deg C, 1h, 2) 20 deg C, 2h, 3) refrigerator, overnight;
DOI:10.1021/jo00008a037

Reference yield:

: 1121-63-7
cyclohepta-3,5-dien-1-ol

: 132622-36-7
1β-((tert-butyldimethylsilyl)oxy)-4α-(p-toluenesulfonamido)-2,3-epoxy-6α-(benzyloxy)cycloheptane

Guidance literature:: Multi-step reaction with 6 steps

1: NaH / tetrahydrofuran / 15 h / 50 °C

2: 63 percent / LiCl, p-benzoquinone, glacial acetic acid / Pd(OAc)2 / acetic acid / 36 h

3: 79 percent / dimethylsulfoxide / 3 h / 80 °C

4: 84 percent / 2M NaOH / methanol / 4 h / Heating

5: 94 percent / imidazole / dimethylformamide / 4 h / 0 °C

6: 96 percent / m-CPBA / CHCl₃ / 1) 0 deg C, 1h, 2) 20 deg C, 2h, 3) refrigerator, overnight

With 1H-imidazole; sodium hydroxide; sodium hydride; acetic acid; 3-chloro-benzenecarboperoxoic acid; p-benzoquinone; lithium chloride; palladium diacetate; In tetrahydrofuran; methanol; chloroform; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jo00008a037

Reference yield:

: 100-39-0
benzyl bromide

: 132622-36-7
1β-((tert-butyldimethylsilyl)oxy)-4α-(p-toluenesulfonamido)-2,3-epoxy-6α-(benzyloxy)cycloheptane

Guidance literature:: Multi-step reaction with 6 steps

1: NaH / tetrahydrofuran / 15 h / 50 °C

2: 63 percent / LiCl, p-benzoquinone, glacial acetic acid / Pd(OAc)2 / acetic acid / 36 h

3: 79 percent / dimethylsulfoxide / 3 h / 80 °C

4: 84 percent / 2M NaOH / methanol / 4 h / Heating

5: 94 percent / imidazole / dimethylformamide / 4 h / 0 °C

6: 96 percent / m-CPBA / CHCl₃ / 1) 0 deg C, 1h, 2) 20 deg C, 2h, 3) refrigerator, overnight

With 1H-imidazole; sodium hydroxide; sodium hydride; acetic acid; 3-chloro-benzenecarboperoxoic acid; p-benzoquinone; lithium chloride; palladium diacetate; In tetrahydrofuran; methanol; chloroform; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jo00008a037