tert-Butyl-[(2R,3R,4R,4aS,9aS)-2-(2-chloro-2-phenylsulfanyl-ethyl)-4-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-yloxy]-dimethyl-silane

Base Information

• Chemical Name: tert-Butyl-[(2R,3R,4R,4aS,9aS)-2-(2-chloro-2-phenylsulfanyl-ethyl)-4-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-yloxy]-dimethyl-silane
• CAS No.: 917896-65-2
• Molecular Formula: C₃₄H₄₃ClO₄SSi
• Molecular Weight: 611.318
• Mol file: 917896-65-2.mol

Synonyms:tert-Butyl-[(2R,3R,4R,4aS,9aS)-2-(2-chloro-2-phenylsulfanyl-ethyl)-4-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-yloxy]-dimethyl-silane

Chemical Property of tert-Butyl-[(2R,3R,4R,4aS,9aS)-2-(2-chloro-2-phenylsulfanyl-ethyl)-4-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-yloxy]-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-[(2R,3R,4R,4aS,9aS)-2-(2-chloro-2-phenylsulfanyl-ethyl)-4-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-yloxy]-dimethyl-silane

There total 10 articles about tert-Butyl-[(2R,3R,4R,4aS,9aS)-2-(2-chloro-2-phenylsulfanyl-ethyl)-4-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-yloxy]-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:

tert-Butyl-dimethyl-[(2R,3R,4R,4aS,9aS)-4-(naphthalen-2-ylmethoxy)-2-(2-phenylsulfanyl-ethyl)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-yloxy]-silane (917896-75-4) → tert-Butyl-[(2R,3R,4R,4aS,9aS)-2-(2-chloro-2-phenylsulfanyl-ethyl)-4-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-yloxy]-dimethyl-silane (917896-65-2)

Guidance literature:

With N-chloro-succinimide; In tetrachloromethane; dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/ol062350h

Reference yield:

(2R,3R,4S,4aS,9aS)-2-Hydroxymethyl-4-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-ol (917896-71-0) → tert-Butyl-[(2R,3R,4R,4aS,9aS)-2-(2-chloro-2-phenylsulfanyl-ethyl)-4-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-yloxy]-dimethyl-silane (917896-65-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 95 percent / I₂; imidazole; PPh₃ / tetrahydrofuran / 3 h / 20 °C

2: 98 percent / dimethylsulfoxide / 24 h / 40 °C

3: 88 percent / imidazole / dimethylformamide / 72 h / 40 °C

4: DIBAL / CH₂Cl₂; hexane / 0.67 h / -78 °C

5: 740 mg / NaBH₄ / methanol; CH₂Cl₂ / 1.5 h / 0 °C

6: 99 percent / pyridine; n-Bu₃P / 0.67 h / 20 °C

7: NCS / CCl₄; CH₂Cl₂ / 1 h / 20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; N-chloro-succinimide; tributylphosphine; iodine; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; methanol; tetrachloromethane; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/ol062350h

Reference yield:

(2S,3S,4S,4aS,9aS)-2-Iodomethyl-4-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-ol (917896-94-7) → tert-Butyl-[(2R,3R,4R,4aS,9aS)-2-(2-chloro-2-phenylsulfanyl-ethyl)-4-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-yloxy]-dimethyl-silane (917896-65-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / dimethylsulfoxide / 24 h / 40 °C

2: 88 percent / imidazole / dimethylformamide / 72 h / 40 °C

3: DIBAL / CH₂Cl₂; hexane / 0.67 h / -78 °C

4: 740 mg / NaBH₄ / methanol; CH₂Cl₂ / 1.5 h / 0 °C

5: 99 percent / pyridine; n-Bu₃P / 0.67 h / 20 °C

6: NCS / CCl₄; CH₂Cl₂ / 1 h / 20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; N-chloro-succinimide; tributylphosphine; diisobutylaluminium hydride; In methanol; tetrachloromethane; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/ol062350h

upstream raw materials:

tert-Butyl-dimethyl-[(2R,3R,4R,4aS,9aS)-4-(naphthalen-2-ylmethoxy)-2-(2-phenylsulfanyl-ethyl)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-yloxy]-silane

(2R,3R,4S,4aS,9aS)-2-Hydroxymethyl-4-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-ol

(2S,3S,4S,4aS,9aS)-2-Iodomethyl-4-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-ol

[(2R,3R,4S,4aS,9aS)-3-Hydroxy-4-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-yl]-acetonitrile