[(3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-2,3,6,7-tetrahydro-oxepin-2-yl]-propynoic acid methyl ester

Base Information

Chemical Name:[(3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-2,3,6,7-tetrahydro-oxepin-2-yl]-propynoic acid methyl ester
CAS No.:482647-09-6
Molecular Formula:C₄₁H₄₄O₆Si
Molecular Weight:660.882
Hs Code.:

Synonyms:[(3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-2,3,6,7-tetrahydro-oxepin-2-yl]-propynoic acid methyl ester

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Chemical Property of [(3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-2,3,6,7-tetrahydro-oxepin-2-yl]-propynoic acid methyl ester

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Technology Process of [(3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-2,3,6,7-tetrahydro-oxepin-2-yl]-propynoic acid methyl ester

There total 9 articles about [(3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-2,3,6,7-tetrahydro-oxepin-2-yl]-propynoic acid methyl ester 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: 76.0%

: 79-22-1
methyl chloroformate

: 482647-08-5
((3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-2-ethynyl-2,3,6,7-tetrahydro-oxepin-3-yloxy)-tert-butyl-diphenyl-silane

: 482647-09-6
[(3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-2,3,6,7-tetrahydro-oxepin-2-yl]-propynoic acid methyl ester

Guidance literature:: With n-butyllithium; at -78 ℃; for 3h;
DOI:10.1055/s-2002-34904

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 482647-09-6
[(3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-2,3,6,7-tetrahydro-oxepin-2-yl]-propynoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 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

7: 91 percent / NaH; TBAI / tetrahydrofuran / 9 h / 25 °C

8: 76 percent / BuLi / 3 h / -78 °C

With 1H-imidazole; n-butyllithium; oxalyl dichloride; methyllithium; tetra-(n-butyl)ammonium iodide; sodium hydride; 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

: 482647-09-6
[(3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-2,3,6,7-tetrahydro-oxepin-2-yl]-propynoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 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

7: 91 percent / NaH; TBAI / tetrahydrofuran / 9 h / 25 °C

8: 76 percent / BuLi / 3 h / -78 °C

With 1H-imidazole; n-butyllithium; oxalyl dichloride; methyllithium; tetra-(n-butyl)ammonium iodide; sodium hydride; 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