(S,S_S)-3-[(tert-butyldimethylsilyloxy)methyl]phenyl-2,3-dihydrobenzo[d]isothiazole-1-oxide

Base Information

• Chemical Name: (S,S_S)-3-[(tert-butyldimethylsilyloxy)methyl]phenyl-2,3-dihydrobenzo[d]isothiazole-1-oxide
• CAS No.: 1609692-27-4
• Molecular Formula: C₂₀H₂₇NO₂SSi
• Molecular Weight: 373.591

Synonyms:(S,S_S)-3-[(tert-butyldimethylsilyloxy)methyl]phenyl-2,3-dihydrobenzo[d]isothiazole-1-oxide

Chemical Property of (S,S_S)-3-[(tert-butyldimethylsilyloxy)methyl]phenyl-2,3-dihydrobenzo[d]isothiazole-1-oxide

Chemical Property:

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Technology Process of (S,S_S)-3-[(tert-butyldimethylsilyloxy)methyl]phenyl-2,3-dihydrobenzo[d]isothiazole-1-oxide

There total 3 articles about (S,S_S)-3-[(tert-butyldimethylsilyloxy)methyl]phenyl-2,3-dihydrobenzo[d]isothiazole-1-oxide 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: 86.0%

(S,RS)-N-[(2-bromophenyl)(3-{[(tert-butyldimethylsilyl)oxy]methyl}phenyl)methyl]-2-methylpropane-2-sulfinamide (1609692-17-2) → (S,SS)-3-[(tert-butyldimethylsilyloxy)methyl]phenyl-2,3-dihydrobenzo[d]isothiazole-1-oxide (1609692-27-4)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 110 ℃; for 6h;

DOI:10.1039/c4cc01831a

Reference yield:

(3-(((tert-butyldimethylsilyl)oxy)methyl)phenyl)magnesium bromide (118892-45-8) → (S,SS)-3-[(tert-butyldimethylsilyloxy)methyl]phenyl-2,3-dihydrobenzo[d]isothiazole-1-oxide (1609692-27-4)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 3 h / -48 °C

2: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 6 h / 110 °C

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In tetrahydrofuran; toluene;

DOI:10.1039/c4cc01831a

Reference yield:

(R)-N-(2-bromobenzyliden)-N-(tert-butanesulfinyl)amine (1015198-51-2) → (S,SS)-3-[(tert-butyldimethylsilyloxy)methyl]phenyl-2,3-dihydrobenzo[d]isothiazole-1-oxide (1609692-27-4)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 3 h / -48 °C

2: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 6 h / 110 °C

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In tetrahydrofuran; toluene;

DOI:10.1039/c4cc01831a

upstream raw materials:

(S,R_S)-N-[(2-bromophenyl)(3-{[(tert-butyldimethylsilyl)oxy]methyl}phenyl)methyl]-2-methylpropane-2-sulfinamide

(3-(((tert-butyldimethylsilyl)oxy)methyl)phenyl)magnesium bromide

(R)-N-(2-bromobenzyliden)-N-(tert-butanesulfinyl)amine

Downstream raw materials:

(S)-3-(3-{[(tert-butyldimethylsilyl)oxy]methyl}phenyl)-2,3-dihydrobenzo[d]isothiazole-1,1-dioxide

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