3-[(3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-2,3,6,7-tetrahydro-oxepin-2-yl]-prop-2-yn-1-ol

Base Information

• Chemical Name: 3-[(3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-2,3,6,7-tetrahydro-oxepin-2-yl]-prop-2-yn-1-ol
• CAS No.: 482647-10-9
• Molecular Formula: C₄₀H₄₄O₅Si
• Molecular Weight: 632.872

Synonyms:3-[(3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-2,3,6,7-tetrahydro-oxepin-2-yl]-prop-2-yn-1-ol

Chemical Property of 3-[(3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-2,3,6,7-tetrahydro-oxepin-2-yl]-prop-2-yn-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of 3-[(3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-2,3,6,7-tetrahydro-oxepin-2-yl]-prop-2-yn-1-ol

There total 10 articles about 3-[(3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-2,3,6,7-tetrahydro-oxepin-2-yl]-prop-2-yn-1-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: 98.0%

[(3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-2,3,6,7-tetrahydro-oxepin-2-yl]-propynoic acid methyl ester (482647-09-6) → 3-[(3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-2,3,6,7-tetrahydro-oxepin-2-yl]-prop-2-yn-1-ol (482647-10-9)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 4h;

DOI:10.1055/s-2002-34904

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 3-[(3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-2,3,6,7-tetrahydro-oxepin-2-yl]-prop-2-yn-1-ol (482647-10-9)

Guidance literature:

Multi-step reaction with 9 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

9: 98 percent / DIBALH / CH₂Cl₂ / 4 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:

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) → 3-[(3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-2,3,6,7-tetrahydro-oxepin-2-yl]-prop-2-yn-1-ol (482647-10-9)

Guidance literature:

Multi-step reaction with 9 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

9: 98 percent / DIBALH / CH₂Cl₂ / 4 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

upstream 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

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

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

Downstream raw materials:

(Z)-3-[(2S,3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-2,3,6,7-tetrahydro-oxepin-2-yl]-prop-2-en-1-ol

(Z)-3-[(2S,3R,6S,7R)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-2,3,6,7-tetrahydro-oxepin-2-yl]-propenal

(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

(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

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