(4aR,6S,7R,8aS)-6-{4-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-ynyl}-7-(tert-butyl-dimethyl-silanyloxy)-2,2,4a-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Base Information

Chemical Name:(4aR,6S,7R,8aS)-6-{4-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-ynyl}-7-(tert-butyl-dimethyl-silanyloxy)-2,2,4a-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine
CAS No.:476688-33-2
Molecular Formula:C₄₇H₇₄O₈Si₂
Molecular Weight:823.271
Hs Code.:

(4aR,6S,7R,8aS)-6-{4-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-ynyl}-7-(tert-butyl-dimethyl-silanyloxy)-2,2,4a-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Synonyms:(4aR,6S,7R,8aS)-6-{4-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-ynyl}-7-(tert-butyl-dimethyl-silanyloxy)-2,2,4a-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine

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Chemical Property of (4aR,6S,7R,8aS)-6-{4-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-ynyl}-7-(tert-butyl-dimethyl-silanyloxy)-2,2,4a-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine

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Technology Process of (4aR,6S,7R,8aS)-6-{4-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-ynyl}-7-(tert-butyl-dimethyl-silanyloxy)-2,2,4a-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine

There total 16 articles about (4aR,6S,7R,8aS)-6-{4-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-ynyl}-7-(tert-butyl-dimethyl-silanyloxy)-2,2,4a-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine 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: 75.0%

: 476688-32-1
Trifluoro-methanesulfonic acid (2R,3S,5R,6S)-5-benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester

: 476687-91-9
tert-Butyl-dimethyl-((4aR,6S,7R,8aS)-2,2,4a-trimethyl-6-prop-2-ynyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane

: 476688-33-2
(4aR,6S,7R,8aS)-6-{4-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-ynyl}-7-(tert-butyl-dimethyl-silanyloxy)-2,2,4a-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Guidance literature:: tert-Butyl-dimethyl-((4aR,6S,7R,8aS)-2,2,4a-trimethyl-6-prop-2-ynyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane; With N,N,N,N,N,N-hexamethylphosphoric triamide; tert.-butyl lithium; In tetrahydrofuran; at -78 ℃;

Trifluoro-methanesulfonic acid (2R,3S,5R,6S)-5-benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester; Further stages.;
DOI:10.1021/ol026804w

Reference yield:

: 361534-73-8
(2S,4aS,6R,7S,8aR)-6-Hydroxymethyl-6-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 476688-33-2
(4aR,6S,7R,8aS)-6-{4-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-ynyl}-7-(tert-butyl-dimethyl-silanyloxy)-2,2,4a-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Guidance literature:: Multi-step reaction with 6 steps

1.1: 94 percent / CSA / dimethylformamide / 20 °C

2.1: 99 percent / H₂ / Pd(OH)2 / ethyl acetate / 20 °C

3.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

3.2: CH₂Cl₂ / -78 °C

4.1: n-BuLi / tetrahydrofuran / -78 °C

5.1: 83 percent / K₂CO₃ / methanol / 20 °C

6.1: 75 percent / t-BuLi; HMPA / tetrahydrofuran / -78 °C

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; camphor-10-sulfonic acid; hydrogen; tert.-butyl lithium; potassium carbonate; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/ol026804w

Reference yield:

: 476688-20-7
(4aR,7S,8aR,9aS,10aS)-2,2,4a-Trimethyl-7-phenyl-hexahydro-1,3,6,8,10-pentaoxa-anthracene

: 476688-33-2
(4aR,6S,7R,8aS)-6-{4-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-ynyl}-7-(tert-butyl-dimethyl-silanyloxy)-2,2,4a-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 99 percent / H₂ / Pd(OH)2 / ethyl acetate / 20 °C

2.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

2.2: CH₂Cl₂ / -78 °C

3.1: n-BuLi / tetrahydrofuran / -78 °C

4.1: 83 percent / K₂CO₃ / methanol / 20 °C

5.1: 75 percent / t-BuLi; HMPA / tetrahydrofuran / -78 °C

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; hydrogen; tert.-butyl lithium; potassium carbonate; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;
DOI:10.1021/ol026804w