(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

Base Information

Chemical Name:(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
CAS No.:482646-94-6
Molecular Formula:C₆₁H₆₅BrO₁₁
Molecular Weight:1054.08
Hs Code.:

(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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Suppliers and Price of (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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Chemical Property of (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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Technology Process of (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

There total 24 articles about (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 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:

: 483340-40-5
(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

: 482646-94-6
(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

Guidance literature:: With trifluoroacetic acid; In tetrahydrofuran; at 25 ℃; for 60h;
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

: 482646-94-6
(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

Guidance literature:: Multi-step reaction with 14 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

13.1: 91 percent / TBAF / tetrahydrofuran / 2.5 h / 25 °C

14.1: aq. TFA / tetrahydrofuran / 60 h / 25 °C

With 1H-imidazole; quinoline; n-butyllithium; oxalyl dichloride; (COCl₂)2; tetrabutyl ammonium fluoride; 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:

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

: 482646-94-6
(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

Guidance literature:: Multi-step reaction with 8 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

7.1: 91 percent / TBAF / tetrahydrofuran / 2.5 h / 25 °C

8.1: aq. TFA / tetrahydrofuran / 60 h / 25 °C

With quinoline; n-butyllithium; (COCl₂)2; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; ethanol; dichloromethane; 5.1: Swern oxidation;
DOI:10.1055/s-2002-34904