(2S,5R,6R,7Z)-8-<(2S,3R,5S,6S)-6-<(1S,2R)-1-ethyl-2-hydroxybutyl>-2-methoxy-3,5-dimethyltetrahydropyran-2-yl>-2-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-6-(4-methoxybenzyloxy)oct-7-ene-2,5-diol

Base Information

Chemical Name:(2S,5R,6R,7Z)-8-<(2S,3R,5S,6S)-6-<(1S,2R)-1-ethyl-2-hydroxybutyl>-2-methoxy-3,5-dimethyltetrahydropyran-2-yl>-2-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-6-(4-methoxybenzyloxy)oct-7-ene-2,5-diol
CAS No.:126454-09-9
Molecular Formula:C₄₆H₇₂O₁₀
Molecular Weight:785.072
Hs Code.:

(2S,5R,6R,7Z)-8-<(2S,3R,5S,6S)-6-<(1S,2R)-1-ethyl-2-hydroxybutyl>-2-methoxy-3,5-dimethyltetrahydropyran-2-yl>-2-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-6-(4-methoxybenzyloxy)oct-7-ene-2,5-diol

Synonyms:(2S,5R,6R,7Z)-8-<(2S,3R,5S,6S)-6-<(1S,2R)-1-ethyl-2-hydroxybutyl>-2-methoxy-3,5-dimethyltetrahydropyran-2-yl>-2-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-6-(4-methoxybenzyloxy)oct-7-ene-2,5-diol

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Chemical Property of (2S,5R,6R,7Z)-8-<(2S,3R,5S,6S)-6-<(1S,2R)-1-ethyl-2-hydroxybutyl>-2-methoxy-3,5-dimethyltetrahydropyran-2-yl>-2-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-6-(4-methoxybenzyloxy)oct-7-ene-2,5-diol

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Technology Process of (2S,5R,6R,7Z)-8-<(2S,3R,5S,6S)-6-<(1S,2R)-1-ethyl-2-hydroxybutyl>-2-methoxy-3,5-dimethyltetrahydropyran-2-yl>-2-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-6-(4-methoxybenzyloxy)oct-7-ene-2,5-diol

There total 20 articles about (2S,5R,6R,7Z)-8-<(2S,3R,5S,6S)-6-<(1S,2R)-1-ethyl-2-hydroxybutyl>-2-methoxy-3,5-dimethyltetrahydropyran-2-yl>-2-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-6-(4-methoxybenzyloxy)oct-7-ene-2,5-diol 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: 71.0%

: 120269-87-6,126454-19-1
(2S,5R,6R)-8-<(2RS,3R,5S,6S)-6-<(1S,2R)-1-ethyl-2-hydroxybutyl>-2-methoxy-3,5-dimethyltetrahydropyran-2-yl>-2-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-6-(4-methoxybenzyloxy)oct-7-yne-2,5-diol

: 120269-88-7
(2S,5R,6R,7Z)-8-<(2R,3R,5S,6S)-6-<(1S,2R)-1-ethyl-2-hydroxybutyl>-2-methoxy-3,5-dimethyltetrahydropyran-2-yl>-2-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-6-(4-methoxybenzyloxy)oct-7-ene-2,5-diol

: 126454-09-9
(2S,5R,6R,7Z)-8-<(2S,3R,5S,6S)-6-<(1S,2R)-1-ethyl-2-hydroxybutyl>-2-methoxy-3,5-dimethyltetrahydropyran-2-yl>-2-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-6-(4-methoxybenzyloxy)oct-7-ene-2,5-diol

Guidance literature:: With hydrogen; Lindlar's catalyst; Lindlar catalyst; In methanol; Ambient temperature;
DOI:10.1248/cpb.37.1717

Reference yield:

: 120269-75-2
(2R,3R,6S)-6-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-3,6-bis(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)heptan-1-ol

: 126454-09-9
(2S,5R,6R,7Z)-8-<(2S,3R,5S,6S)-6-<(1S,2R)-1-ethyl-2-hydroxybutyl>-2-methoxy-3,5-dimethyltetrahydropyran-2-yl>-2-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-6-(4-methoxybenzyloxy)oct-7-ene-2,5-diol

Guidance literature:: Multi-step reaction with 13 steps

1: 1) DMSO, (COCl₂)2, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 2) CH₂Cl₂, -78 to -15 deg C

2: 96 percent / Ph₃P / benzene / 0.5 h / 80 °C

3: 84 percent / n-BuLi / hexane; tetrahydrofuran / -78 - -20 °C

4: 1) NaH / 1) DMF, 2) DMF, 50 deg C, 2 h

5: MeOH, CSA / 0.25 h / Ambient temperature

6: 1) DMSO, (COCl₂)2, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 2) CH₂Cl₂, -78 to -15 deg C

7: 88 percent / Ph₃P / CH₂Cl₂ / 0.33 h / -78 °C

8: 83 percent / LDA / tetrahydrofuran / 0.67 h / -70 °C

9: 1) n-BuLi / 1) THF, hexane, -78 deg C, 40 min, 2) THF, hexane, Et₂O, -78 to -15 deg C, 2 h

10: 1) DMSO, (COCl)2, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 2) CH₂Cl₂, -78 to -15 deg C

11: CSA / 1.83 h / Ambient temperature

12: n-Bu₄NF / tetrahydrofuran / 70 °C

13: 18 percent / hydrogen / Pd/CaCO₃, Pb (Lindlar cat.) / methanol / Ambient temperature

With methanol; n-butyllithium; oxalyl dichloride; (COCl₂)2; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium diisopropyl amide; Lindlar's catalyst; Pb (Lindlar cat.); In tetrahydrofuran; methanol; hexane; dichloromethane; benzene;
DOI:10.1248/cpb.37.1717

Reference yield:

: 120269-85-4
(3R,4R,7S)-4,7-bis(tert-butyldimethylsilyloxy)-7-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-3-(4-methoxybenzyloxy)oct-1-yne

: 126454-09-9
(2S,5R,6R,7Z)-8-<(2S,3R,5S,6S)-6-<(1S,2R)-1-ethyl-2-hydroxybutyl>-2-methoxy-3,5-dimethyltetrahydropyran-2-yl>-2-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-6-(4-methoxybenzyloxy)oct-7-ene-2,5-diol

Guidance literature:: Multi-step reaction with 5 steps

1: 1) n-BuLi / 1) THF, hexane, -78 deg C, 40 min, 2) THF, hexane, Et₂O, -78 to -15 deg C, 2 h

2: 1) DMSO, (COCl)2, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 2) CH₂Cl₂, -78 to -15 deg C

3: CSA / 1.83 h / Ambient temperature

4: n-Bu₄NF / tetrahydrofuran / 70 °C

5: 18 percent / hydrogen / Pd/CaCO₃, Pb (Lindlar cat.) / methanol / Ambient temperature

With n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; Lindlar's catalyst; Pb (Lindlar cat.); In tetrahydrofuran; methanol;
DOI:10.1248/cpb.37.1717