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

Base Information

• Chemical Name: 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
• CAS No.: 483340-39-2
• Molecular Formula: C₇₉H₈₉BrO₁₁S₂Si
• Molecular Weight: 1386.69

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 22 articles about 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 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:

tert-butylchlorodiphenylsilane (58479-61-1) → 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 (483340-39-2)

Guidance literature:

Multi-step reaction with 12 steps

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

2.1: DIBALH / CH₂Cl₂ / 1 h / -78 °C

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

4.1: PPh₃ / CH₂Cl₂ / 6 h / -78 °C

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

6.1: 69 percent / aq. TFA / tetrahydrofuran / 84 h / 25 °C

7.1: 91 percent / NaH; TBAI / tetrahydrofuran / 9 h / 25 °C

8.1: 76 percent / BuLi / 3 h / -78 °C

9.1: 98 percent / DIBALH / CH₂Cl₂ / 4 h / -78 °C

10.1: 98 percent / H₂; quinoline / Lindlar catalyst / ethanol / 72 h / 25 °C

11.1: (COCl₂)2; DMSO; Et₃N / CH₂Cl₂ / 0.83 h / -78 - -47 °C

12.1: LDA / 0.25 h / -78 °C

12.2: 1 h / -78 °C

With 1H-imidazole; quinoline; n-butyllithium; oxalyl dichloride; (COCl₂)2; methyllithium; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; trifluoroacetic acid; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 3.1: Swern oxidation / 4.1: Wittig reaction / 11.1: Swern oxidation;

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) → 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 (483340-39-2)

Guidance literature:

Multi-step reaction with 12 steps

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

2.1: DIBALH / CH₂Cl₂ / 1 h / -78 °C

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

4.1: PPh₃ / CH₂Cl₂ / 6 h / -78 °C

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

6.1: 69 percent / aq. TFA / tetrahydrofuran / 84 h / 25 °C

7.1: 91 percent / NaH; TBAI / tetrahydrofuran / 9 h / 25 °C

8.1: 76 percent / BuLi / 3 h / -78 °C

9.1: 98 percent / DIBALH / CH₂Cl₂ / 4 h / -78 °C

10.1: 98 percent / H₂; quinoline / Lindlar catalyst / ethanol / 72 h / 25 °C

11.1: (COCl₂)2; DMSO; Et₃N / CH₂Cl₂ / 0.83 h / -78 - -47 °C

12.1: LDA / 0.25 h / -78 °C

12.2: 1 h / -78 °C

With 1H-imidazole; quinoline; n-butyllithium; oxalyl dichloride; (COCl₂)2; methyllithium; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; trifluoroacetic acid; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 3.1: Swern oxidation / 4.1: Wittig reaction / 11.1: Swern oxidation;

DOI:10.1055/s-2002-34904

Reference yield:

(2R,3S,6R)-6-(tert-Butyl-diphenyl-silanyloxy)-7-ethynyl-2-hydroxymethyl-2,3,6,7-tetrahydro-oxepin-3-ol (482647-07-4) → 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 (483340-39-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 91 percent / NaH; TBAI / tetrahydrofuran / 9 h / 25 °C

2.1: 76 percent / BuLi / 3 h / -78 °C

3.1: 98 percent / DIBALH / CH₂Cl₂ / 4 h / -78 °C

4.1: 98 percent / H₂; quinoline / Lindlar catalyst / ethanol / 72 h / 25 °C

5.1: (COCl₂)2; DMSO; Et₃N / CH₂Cl₂ / 0.83 h / -78 - -47 °C

6.1: LDA / 0.25 h / -78 °C

6.2: 1 h / -78 °C

With quinoline; n-butyllithium; (COCl₂)2; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; ethanol; dichloromethane; 5.1: Swern oxidation;

DOI:10.1055/s-2002-34904

upstream 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]-propenal

(2S,3S,4R,5R,6R)-3,4-Bis-benzyloxy-2-(2-benzyloxy-ethyl)-5-(4-bromo-benzyloxy)-6-(2-methanesulfinyl-2-methylsulfanyl-ethyl)-tetrahydro-pyran

4-bromobenzenemethanol

benzyl bromide

Downstream raw materials:

(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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