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

Base Information

• Chemical Name: ((3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-2-ethynyl-2,3,6,7-tetrahydro-oxepin-3-yloxy)-tert-butyl-diphenyl-silane
• CAS No.: 482647-08-5
• Molecular Formula: C₃₉H₄₂O₄Si
• Molecular Weight: 602.846

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

Chemical Property of ((3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-2-ethynyl-2,3,6,7-tetrahydro-oxepin-3-yloxy)-tert-butyl-diphenyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of ((3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-2-ethynyl-2,3,6,7-tetrahydro-oxepin-3-yloxy)-tert-butyl-diphenyl-silane

There total 8 articles about ((3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-2-ethynyl-2,3,6,7-tetrahydro-oxepin-3-yloxy)-tert-butyl-diphenyl-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: 91.0%

benzyl bromide (100-39-0) + (2R,3S,6R)-6-(tert-Butyl-diphenyl-silanyloxy)-7-ethynyl-2-hydroxymethyl-2,3,6,7-tetrahydro-oxepin-3-ol (482647-07-4) → ((3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-2-ethynyl-2,3,6,7-tetrahydro-oxepin-3-yloxy)-tert-butyl-diphenyl-silane (482647-08-5)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 25 ℃; for 9h;

DOI:10.1055/s-2002-34904

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → ((3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-2-ethynyl-2,3,6,7-tetrahydro-oxepin-3-yloxy)-tert-butyl-diphenyl-silane (482647-08-5)

Guidance literature:

Multi-step reaction with 7 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

With 1H-imidazole; 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:

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 (475641-58-8) → ((3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-2-ethynyl-2,3,6,7-tetrahydro-oxepin-3-yloxy)-tert-butyl-diphenyl-silane (482647-08-5)

Guidance literature:

Multi-step reaction with 7 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

With 1H-imidazole; 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

upstream raw materials:

benzyl bromide

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

tert-butylchlorodiphenylsilane

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

Downstream raw materials:

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

1-[6-benzyloxy-7-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-2,3,6,7-tetrahydro-oxepin-2-yl]-5-[4,5-bis-benzyloxy-6-(2-benzyloxy-ethyl)-3-(4-bromo-benzyloxy)-tetrahydro-pyran-2-yl]-4-methanesulfinyl-4-methylsulfanyl-pent-1-en-3-ol

(2S,3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-2-{(Z)-5-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-(2-benzyloxy-ethyl)-3-(4-bromo-benzyloxy)-tetrahydro-pyran-2-yl]-3-hydroxy-4-methanesulfinyl-4-methylsulfanyl-pent-1-enyl}-2,3,6,7-tetrahydro-oxepin-3-ol

(Z)-5-((2S,3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-3-hydroxy-2,3,6,7-tetrahydro-oxepin-2-yl)-1-[(2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-(2-benzyloxy-ethyl)-3-(4-bromo-benzyloxy)-tetrahydro-pyran-2-yl]-3-hydroxy-pent-4-en-2-one

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