(4aR,6S,7R,8aS)-6-[4-((2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-6-methyl-3-triethylsilanyloxy-oxepan-2-yl)-but-2-ynyl]-2,2-di-tert-butyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-2-sila-naphthalene

Base Information

Chemical Name:(4aR,6S,7R,8aS)-6-[4-((2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-6-methyl-3-triethylsilanyloxy-oxepan-2-yl)-but-2-ynyl]-2,2-di-tert-butyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-2-sila-naphthalene
CAS No.:440635-16-5
Molecular Formula:C₅₂H₈₆O₈Si₃
Molecular Weight:923.507
Hs Code.:

(4aR,6S,7R,8aS)-6-[4-((2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-6-methyl-3-triethylsilanyloxy-oxepan-2-yl)-but-2-ynyl]-2,2-di-tert-butyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-2-sila-naphthalene

Synonyms:(4aR,6S,7R,8aS)-6-[4-((2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-6-methyl-3-triethylsilanyloxy-oxepan-2-yl)-but-2-ynyl]-2,2-di-tert-butyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-2-sila-naphthalene

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Chemical Property of (4aR,6S,7R,8aS)-6-[4-((2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-6-methyl-3-triethylsilanyloxy-oxepan-2-yl)-but-2-ynyl]-2,2-di-tert-butyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-2-sila-naphthalene

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Technology Process of (4aR,6S,7R,8aS)-6-[4-((2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-6-methyl-3-triethylsilanyloxy-oxepan-2-yl)-but-2-ynyl]-2,2-di-tert-butyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-2-sila-naphthalene

There total 27 articles about (4aR,6S,7R,8aS)-6-[4-((2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-6-methyl-3-triethylsilanyloxy-oxepan-2-yl)-but-2-ynyl]-2,2-di-tert-butyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-2-sila-naphthalene 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: 95.0%

: 79271-56-0
triethylsilyl trifluoromethyl sulfonate

: (4aR,6S,7R,8aS)-6-[4-((2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-3-hydroxy-6-methyl-oxepan-2-yl)-but-2-ynyl]-2,2-di-tert-butyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-ol

: 440635-16-5
(4aR,6S,7R,8aS)-6-[4-((2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-6-methyl-3-triethylsilanyloxy-oxepan-2-yl)-but-2-ynyl]-2,2-di-tert-butyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-2-sila-naphthalene

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1016/S0040-4020(02)00038-8

Reference yield:

: 391235-78-2
(1S,6R,8S)-8-(benzyloxy)methyl-3,3-di-tert-butyl-2,4,7-trioxa-3-silabicyclo[4.4.0]deca-9-one

: 440635-16-5
(4aR,6S,7R,8aS)-6-[4-((2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-6-methyl-3-triethylsilanyloxy-oxepan-2-yl)-but-2-ynyl]-2,2-di-tert-butyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-2-sila-naphthalene

Guidance literature:: Multi-step reaction with 9 steps

1.1: 95 percent / NaBH₄ / CH₂Cl₂; methanol / 0.5 h / -78 °C

2.1: 100 percent / H₂ / 20 percent Pd(OH)2/C / ethyl acetate / 0.67 h / 20 °C

3.1: 2,6-lutidine / tetrahydrofuran / 0.5 h / -78 °C

4.1: 844 mg / 2,6-lutidine / tetrahydrofuran / 1 h / -78 - 0 °C

5.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / 0 °C

5.2: HMPA / tetrahydrofuran / 2.5 h / 0 °C

6.1: 180 mg / aq. KOH / methanol / 1.5 h / 20 °C

7.1: 71 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / -78 - -20 °C

8.1: 93 percent / TsOH*H₂O / CH₂Cl₂; methanol / 7 h / 20 °C

9.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; hydrogen; toluene-4-sulfonic acid; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate;
DOI:10.1016/S0040-4020(02)00038-8

Reference yield:

: 391235-90-8
4-Benzyloxy-3-bromo-1-((4S,5R)-2,2-di-tert-butyl-5-hydroxy-[1,3,2]dioxasilinan-4-yl)-butan-2-one

: 440635-16-5
(4aR,6S,7R,8aS)-6-[4-((2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-6-methyl-3-triethylsilanyloxy-oxepan-2-yl)-but-2-ynyl]-2,2-di-tert-butyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-2-sila-naphthalene

Guidance literature:: Multi-step reaction with 10 steps

1.1: 83 percent / DBU / CH₂Cl₂ / 1 h / 0 °C

2.1: 95 percent / NaBH₄ / CH₂Cl₂; methanol / 0.5 h / -78 °C

3.1: 100 percent / H₂ / 20 percent Pd(OH)2/C / ethyl acetate / 0.67 h / 20 °C

4.1: 2,6-lutidine / tetrahydrofuran / 0.5 h / -78 °C

5.1: 844 mg / 2,6-lutidine / tetrahydrofuran / 1 h / -78 - 0 °C

6.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / 0 °C

6.2: HMPA / tetrahydrofuran / 2.5 h / 0 °C

7.1: 180 mg / aq. KOH / methanol / 1.5 h / 20 °C

8.1: 71 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / -78 - -20 °C

9.1: 93 percent / TsOH*H₂O / CH₂Cl₂; methanol / 7 h / 20 °C

10.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; hydrogen; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate;
DOI:10.1016/S0040-4020(02)00038-8