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

Base Information

Chemical Name:(2S,5R,6R)-2-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-8-<(2RS,3R,5S,6S)-6-<(1S,2R)-1-ethyl-2-hydroxybutyl>-2-methoxy-3,5-dimethyltetrahydropyran-2-yl>-6-(4-methoxybenzyloxy)oct-7-yne-2,5-diol
CAS No.:120269-78-5
Molecular Formula:C₄₅H₆₈O₉
Molecular Weight:753.03
Hs Code.:

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

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

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

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

There total 21 articles about (2S,5R,6R)-2-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-8-<(2RS,3R,5S,6S)-6-<(1S,2R)-1-ethyl-2-hydroxybutyl>-2-methoxy-3,5-dimethyltetrahydropyran-2-yl>-6-(4-methoxybenzyloxy)oct-7-yne-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: 86.0%

: (3R,4S)-4-{(2S,3S,5R,6R)-6-[(3R,4R,7S)-7-((2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-4,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-oct-1-ynyl]-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl}-hexan-3-ol

: 120269-78-5
(2S,5R,6R)-2-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-8-<(2RS,3R,5S,6S)-6-<(1S,2R)-1-ethyl-2-hydroxybutyl>-2-methoxy-3,5-dimethyltetrahydropyran-2-yl>-6-(4-methoxybenzyloxy)oct-7-yne-2,5-diol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 70 ℃; for 5h;
DOI:10.1248/cpb.37.1717

Reference yield:

: 2280-44-6
D-Glucose

: 120269-78-5,120330-28-1
(2S,5R,6R)-2-((2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-8-[(3R,5S,6S)-6-((1S,2R)-1-ethyl-2-hydroxy-butyl)-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl]-6-(4-methoxy-benzyloxy)-oct-7-yne-2,5-diol

Guidance literature:: Multi-step reaction with 7 steps

3: 99 percent / DMSO, (COCl)2, Et₃N / CH₂Cl₂

4: 96 percent / PPh₃ / benzene / 80 °C

5: 84 percent / n-BuLi / tetrahydrofuran / -78 °C

6: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) oxidation

7: 1.) camphorsulfonic acid, 2.) n-Bu₄NF / 1.) room temperature, 2.) dioxane-THF, 65 deg C

With n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; benzene;
DOI:10.1016/S0040-4039(00)80703-0

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

: 120269-78-5,120330-28-1
(2S,5R,6R)-2-((2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-8-[(3R,5S,6S)-6-((1S,2R)-1-ethyl-2-hydroxy-butyl)-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl]-6-(4-methoxy-benzyloxy)-oct-7-yne-2,5-diol

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / DMSO, (COCl)2, Et₃N / CH₂Cl₂

2: 96 percent / PPh₃ / benzene / 80 °C

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

4: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) oxidation

5: 1.) camphorsulfonic acid, 2.) n-Bu₄NF / 1.) room temperature, 2.) dioxane-THF, 65 deg C

With n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; benzene;
DOI:10.1016/S0040-4039(00)80703-0