(2R,3S,6R)-6-(tert-Butyl-diphenyl-silanyloxy)-7-ethynyl-2-hydroxymethyl-2,3,6,7-tetrahydro-oxepin-3-ol

Base Information

Chemical Name:(2R,3S,6R)-6-(tert-Butyl-diphenyl-silanyloxy)-7-ethynyl-2-hydroxymethyl-2,3,6,7-tetrahydro-oxepin-3-ol
CAS No.:482647-07-4
Molecular Formula:C₂₅H₃₀O₄Si
Molecular Weight:422.596
Hs Code.:

Synonyms:(2R,3S,6R)-6-(tert-Butyl-diphenyl-silanyloxy)-7-ethynyl-2-hydroxymethyl-2,3,6,7-tetrahydro-oxepin-3-ol

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Chemical Property of (2R,3S,6R)-6-(tert-Butyl-diphenyl-silanyloxy)-7-ethynyl-2-hydroxymethyl-2,3,6,7-tetrahydro-oxepin-3-ol

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Technology Process of (2R,3S,6R)-6-(tert-Butyl-diphenyl-silanyloxy)-7-ethynyl-2-hydroxymethyl-2,3,6,7-tetrahydro-oxepin-3-ol

There total 7 articles about (2R,3S,6R)-6-(tert-Butyl-diphenyl-silanyloxy)-7-ethynyl-2-hydroxymethyl-2,3,6,7-tetrahydro-oxepin-3-ol 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: 69.0%

: 482647-06-3
tert-Butyl-((2R,4aR,7R,9aS)-6-ethynyl-2-phenyl-4a,6,7,9a-tetrahydro-4H-1,3,5-trioxa-benzocyclohepten-7-yloxy)-diphenyl-silane

: 482647-07-4
(2R,3S,6R)-6-(tert-Butyl-diphenyl-silanyloxy)-7-ethynyl-2-hydroxymethyl-2,3,6,7-tetrahydro-oxepin-3-ol

Guidance literature:: With trifluoroacetic acid; In tetrahydrofuran; at 25 ℃; for 84h;
DOI:10.1055/s-2002-34904

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 482647-07-4
(2R,3S,6R)-6-(tert-Butyl-diphenyl-silanyloxy)-7-ethynyl-2-hydroxymethyl-2,3,6,7-tetrahydro-oxepin-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1: imidazole / dimethylformamide / 22.5 h / 70 °C

2: DIBALH / CH₂Cl₂ / 1 h / -78 °C

3: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.83 h / -78 - -47 °C

4: PPh₃ / CH₂Cl₂ / 6 h / -78 °C

5: MeLi / tetrahydrofuran / 1.75 h / -78 - 25 °C

6: 69 percent / aq. TFA / tetrahydrofuran / 84 h / 25 °C

With 1H-imidazole; oxalyl dichloride; methyllithium; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 3: Swern oxidation / 4: Wittig reaction;
DOI:10.1055/s-2002-34904

Reference yield:

: 475641-58-8
2,2-Dimethyl-propionic acid (2R,4aR,6S,7R,9aS)-7-hydroxy-2-phenyl-4a,6,7,9a-tetrahydro-4H-1,3,5-trioxa-benzocyclohepten-6-ylmethyl ester

: 482647-07-4
(2R,3S,6R)-6-(tert-Butyl-diphenyl-silanyloxy)-7-ethynyl-2-hydroxymethyl-2,3,6,7-tetrahydro-oxepin-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1: imidazole / dimethylformamide / 22.5 h / 70 °C

2: DIBALH / CH₂Cl₂ / 1 h / -78 °C

3: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.83 h / -78 - -47 °C

4: PPh₃ / CH₂Cl₂ / 6 h / -78 °C

5: MeLi / tetrahydrofuran / 1.75 h / -78 - 25 °C

6: 69 percent / aq. TFA / tetrahydrofuran / 84 h / 25 °C

With 1H-imidazole; oxalyl dichloride; methyllithium; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 3: Swern oxidation / 4: Wittig reaction;
DOI:10.1055/s-2002-34904