(E)-(2R,3R,7R)-8-[(7R,8R,8aS)-8-Benzyloxy-7-hydroxy-8-methyl-hexahydro-indolizin-(6Z)-ylidene]-8-iodo-4,7-dimethyl-oct-4-ene-2,3-diol

Base Information

Chemical Name:(E)-(2R,3R,7R)-8-[(7R,8R,8aS)-8-Benzyloxy-7-hydroxy-8-methyl-hexahydro-indolizin-(6Z)-ylidene]-8-iodo-4,7-dimethyl-oct-4-ene-2,3-diol
CAS No.:137895-78-4
Molecular Formula:C₂₆H₃₈INO₄
Molecular Weight:555.497
Hs Code.:

Synonyms:(E)-(2R,3R,7R)-8-[(7R,8R,8aS)-8-Benzyloxy-7-hydroxy-8-methyl-hexahydro-indolizin-(6Z)-ylidene]-8-iodo-4,7-dimethyl-oct-4-ene-2,3-diol

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Chemical Property of (E)-(2R,3R,7R)-8-[(7R,8R,8aS)-8-Benzyloxy-7-hydroxy-8-methyl-hexahydro-indolizin-(6Z)-ylidene]-8-iodo-4,7-dimethyl-oct-4-ene-2,3-diol

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Technology Process of (E)-(2R,3R,7R)-8-[(7R,8R,8aS)-8-Benzyloxy-7-hydroxy-8-methyl-hexahydro-indolizin-(6Z)-ylidene]-8-iodo-4,7-dimethyl-oct-4-ene-2,3-diol

There total 12 articles about (E)-(2R,3R,7R)-8-[(7R,8R,8aS)-8-Benzyloxy-7-hydroxy-8-methyl-hexahydro-indolizin-(6Z)-ylidene]-8-iodo-4,7-dimethyl-oct-4-ene-2,3-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: 81.0%

: 137895-77-3
(7R,8R,8aS)-8-(benzyloxy)-7-<(3R,5E,7R,8R)-3,6-dimethyl-7,8-O-isopropylidene-5-decen-1-ynyl>-8-methyl-6-oxaoctahydroindolidizine

: 137895-78-4
(E)-(2R,3R,7R)-8-[(7R,8R,8aS)-8-Benzyloxy-7-hydroxy-8-methyl-hexahydro-indolizin-(6Z)-ylidene]-8-iodo-4,7-dimethyl-oct-4-ene-2,3-diol

Guidance literature:: With formaldehyd; toluene-4-sulfonic acid; sodium iodide; In acetone; at 100 ℃; for 2h;
DOI:10.1021/ja00027a061

Reference yield:

: 137895-76-2
(S)-2-<(1R,2R,5R,7E,9R,10R)-1-(benzyloxy)-2-hydroxy-9,10-O-isopropylidene-1,5,8-trimethyl-7-undecen-3-ynyl>-1-(cyanomethyl)pyrrolidine

: 137895-78-4
(E)-(2R,3R,7R)-8-[(7R,8R,8aS)-8-Benzyloxy-7-hydroxy-8-methyl-hexahydro-indolizin-(6Z)-ylidene]-8-iodo-4,7-dimethyl-oct-4-ene-2,3-diol

Guidance literature:: Multi-step reaction with 2 steps

1: 94 percent / AgOTf / tetrahydrofuran / 3 h / Ambient temperature

2: 81 percent / NaI, aq. CH₂O, camphorsulphonic acid / acetone / 2 h / 100 °C

With formaldehyd; camphor-10-sulfonic acid; silver trifluoromethanesulfonate; sodium iodide; In tetrahydrofuran; acetone;
DOI:10.1021/ja961640y

Reference yield:

: 137895-75-1
(4R,5R)-2,2,4-trimethyl-5-((R,E)-5-methylhept-2-en-6-yn-2-yl)-1,3-dioxolane

: 137895-78-4
(E)-(2R,3R,7R)-8-[(7R,8R,8aS)-8-Benzyloxy-7-hydroxy-8-methyl-hexahydro-indolizin-(6Z)-ylidene]-8-iodo-4,7-dimethyl-oct-4-ene-2,3-diol

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) n-BuLi / 1.) THF, hexane, -15 deg C, 15 min, 2.) THF, hexane, -78 deg C, 2.5 h

2: 94 percent / AgOTf / tetrahydrofuran / 3 h / Ambient temperature

3: 81 percent / NaI, aq. CH₂O, camphorsulphonic acid / acetone / 2 h / 100 °C

With n-butyllithium; formaldehyd; camphor-10-sulfonic acid; silver trifluoromethanesulfonate; sodium iodide; In tetrahydrofuran; acetone;
DOI:10.1021/ja961640y