[(1R,3S,6R,7S)-5-(2-Benzenesulfonyl-ethyl)-4,8-dioxa-tricyclo[4.2.1.0^3,7]non-5-yloxy]-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: [(1R,3S,6R,7S)-5-(2-Benzenesulfonyl-ethyl)-4,8-dioxa-tricyclo[4.2.1.0^3,7]non-5-yloxy]-tert-butyl-dimethyl-silane
• CAS No.: 136057-82-4
• Molecular Formula: C₂₁H₃₂O₅SSi
• Molecular Weight: 424.634

Synonyms:[(1R,3S,6R,7S)-5-(2-Benzenesulfonyl-ethyl)-4,8-dioxa-tricyclo[4.2.1.0^3,7]non-5-yloxy]-tert-butyl-dimethyl-silane

Chemical Property of [(1R,3S,6R,7S)-5-(2-Benzenesulfonyl-ethyl)-4,8-dioxa-tricyclo[4.2.1.0^3,7]non-5-yloxy]-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

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Technology Process of [(1R,3S,6R,7S)-5-(2-Benzenesulfonyl-ethyl)-4,8-dioxa-tricyclo[4.2.1.0^3,7]non-5-yloxy]-tert-butyl-dimethyl-silane

There total 4 articles about [(1R,3S,6R,7S)-5-(2-Benzenesulfonyl-ethyl)-4,8-dioxa-tricyclo[4.2.1.0^3,7]non-5-yloxy]-tert-butyl-dimethyl-silane 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: 84.0%

chloromethyl phenyl sulfone (7205-98-3) + 1-<<(tert-butyl)dimethylsilyl>oxy>-1-<(1RS,2RS,4RS)-(7-oxabicyclo<2.2.1>hept-5-en-2-yl)oxy>ethene (136057-81-3) → [(1R,3S,6R,7S)-5-(2-Benzenesulfonyl-ethyl)-4,8-dioxa-tricyclo[4.2.1.03,7]non-5-yloxy]-tert-butyl-dimethyl-silane (136057-82-4)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 2h; Irradiation;

DOI:10.1016/0040-4039(91)80814-M

Reference yield:

(1RS,2RS,4RS)-7-oxabicyclo< 2.2.1> hept-5-en-2-ol (114370-27-3,114511-69-2,137819-88-6,141900-15-4) → [(1R,3S,6R,7S)-5-(2-Benzenesulfonyl-ethyl)-4,8-dioxa-tricyclo[4.2.1.03,7]non-5-yloxy]-tert-butyl-dimethyl-silane (136057-82-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / pyridine

2: 90 percent / LDA, HMPA

3: 84 percent / Bu₃SnH, AIBN / benzene / 2 h / Irradiation

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; lithium diisopropyl amide; In benzene;

DOI:10.1016/0040-4039(91)80814-M

Reference yield:

(+/-)-7-oxabicyclo<2.2.1>hept-5-en-2-one (88708-22-9,94482-73-2,94482-75-4,95530-78-2) → [(1R,3S,6R,7S)-5-(2-Benzenesulfonyl-ethyl)-4,8-dioxa-tricyclo[4.2.1.03,7]non-5-yloxy]-tert-butyl-dimethyl-silane (136057-82-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / NaBH₄

2: 86 percent / pyridine

3: 90 percent / LDA, HMPA

4: 84 percent / Bu₃SnH, AIBN / benzene / 2 h / Irradiation

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; lithium diisopropyl amide; In benzene;

DOI:10.1016/0040-4039(91)80814-M

upstream raw materials:

chloromethyl phenyl sulfone

1-<<(tert-butyl)dimethylsilyl>oxy>-1-<(1RS,2RS,4RS)-(7-oxabicyclo<2.2.1>hept-5-en-2-yl)oxy>ethene

(1RS,2RS,4RS)-7-oxabicyclo< 2.2.1> hept-5-en-2-ol

(+/-)-7-oxabicyclo<2.2.1>hept-5-en-2-one

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