tert-butyl-dimethyl-[8-oxo-11-(3,4,5-trimethoxy-phenyl)-5,5a,6,10,10a,11-hexahydro-1,3,7,9-tetraoxa-8λ⁴-thia-cyclohepta[b]cyclopenta[g]naphthalen-5-yloxy]-silane

Base Information

• Chemical Name: tert-butyl-dimethyl-[8-oxo-11-(3,4,5-trimethoxy-phenyl)-5,5a,6,10,10a,11-hexahydro-1,3,7,9-tetraoxa-8λ⁴-thia-cyclohepta[b]cyclopenta[g]naphthalen-5-yloxy]-silane
• CAS No.: 689260-03-5
• Molecular Formula: C₂₈H₃₈O₉SSi
• Molecular Weight: 578.756

Synonyms:tert-butyl-dimethyl-[8-oxo-11-(3,4,5-trimethoxy-phenyl)-5,5a,6,10,10a,11-hexahydro-1,3,7,9-tetraoxa-8λ⁴-thia-cyclohepta[b]cyclopenta[g]naphthalen-5-yloxy]-silane

Chemical Property of tert-butyl-dimethyl-[8-oxo-11-(3,4,5-trimethoxy-phenyl)-5,5a,6,10,10a,11-hexahydro-1,3,7,9-tetraoxa-8λ⁴-thia-cyclohepta[b]cyclopenta[g]naphthalen-5-yloxy]-silane

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Technology Process of tert-butyl-dimethyl-[8-oxo-11-(3,4,5-trimethoxy-phenyl)-5,5a,6,10,10a,11-hexahydro-1,3,7,9-tetraoxa-8λ⁴-thia-cyclohepta[b]cyclopenta[g]naphthalen-5-yloxy]-silane

There total 3 articles about tert-butyl-dimethyl-[8-oxo-11-(3,4,5-trimethoxy-phenyl)-5,5a,6,10,10a,11-hexahydro-1,3,7,9-tetraoxa-8λ⁴-thia-cyclohepta[b]cyclopenta[g]naphthalen-5-yloxy]-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: 78.0%

[8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxol-6-yl]-methanol (689260-01-3) → tert-butyl-dimethyl-[8-oxo-11-(3,4,5-trimethoxy-phenyl)-5,5a,6,10,10a,11-hexahydro-1,3,7,9-tetraoxa-8λ4-thia-cyclohepta[b]cyclopenta[g]naphthalen-5-yloxy]-silane (689260-03-5)

Guidance literature:

With dmap; thionyl chloride; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1016/j.bmcl.2003.12.096

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → tert-butyl-dimethyl-[8-oxo-11-(3,4,5-trimethoxy-phenyl)-5,5a,6,10,10a,11-hexahydro-1,3,7,9-tetraoxa-8λ4-thia-cyclohepta[b]cyclopenta[g]naphthalen-5-yloxy]-silane (689260-03-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / imidazole / dimethylformamide

2: 94 percent / lithium aluminum hydride / tetrahydrofuran

3: 78 percent / thionyl chloride; 4-dimethylaminopyridine / CH₂Cl₂ / 1.5 h / 20 °C

With 1H-imidazole; dmap; lithium aluminium tetrahydride; thionyl chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2003.12.096

Reference yield:

(5R,5aR,8aR,9R)-9-((tert-butyldimethylsilyl)oxy)-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one (112711-16-7) → tert-butyl-dimethyl-[8-oxo-11-(3,4,5-trimethoxy-phenyl)-5,5a,6,10,10a,11-hexahydro-1,3,7,9-tetraoxa-8λ4-thia-cyclohepta[b]cyclopenta[g]naphthalen-5-yloxy]-silane (689260-03-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / lithium aluminum hydride / tetrahydrofuran

2: 78 percent / thionyl chloride; 4-dimethylaminopyridine / CH₂Cl₂ / 1.5 h / 20 °C

With dmap; lithium aluminium tetrahydride; thionyl chloride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmcl.2003.12.096

upstream raw materials:

[8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxol-6-yl]-methanol

tert-butyldimethylsilyl chloride

(5R,5aR,8aR,9R)-9-((tert-butyldimethylsilyl)oxy)-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one

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