(1S,5R,6R)-5-hydroxy-3-(hydroxymethyl)-6-((E)-1-iodoprop-1-en-2-yl)-4-oxocyclohex-2-enyl acetate

Base Information

Chemical Name:(1S,5R,6R)-5-hydroxy-3-(hydroxymethyl)-6-((E)-1-iodoprop-1-en-2-yl)-4-oxocyclohex-2-enyl acetate
CAS No.:1110689-55-8
Molecular Formula:C₁₂H₁₅IO₅
Molecular Weight:366.153
Hs Code.:

Synonyms:(1S,5R,6R)-5-hydroxy-3-(hydroxymethyl)-6-((E)-1-iodoprop-1-en-2-yl)-4-oxocyclohex-2-enyl acetate

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Chemical Property of (1S,5R,6R)-5-hydroxy-3-(hydroxymethyl)-6-((E)-1-iodoprop-1-en-2-yl)-4-oxocyclohex-2-enyl acetate

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Technology Process of (1S,5R,6R)-5-hydroxy-3-(hydroxymethyl)-6-((E)-1-iodoprop-1-en-2-yl)-4-oxocyclohex-2-enyl acetate

There total 1 articles about (1S,5R,6R)-5-hydroxy-3-(hydroxymethyl)-6-((E)-1-iodoprop-1-en-2-yl)-4-oxocyclohex-2-enyl acetate 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: 80.0%

: 1110689-60-5
((3S,4R,5R)-3-acetoxy-5-hydroxy-4-((E)-1-iodoprop-1-en-2-yl)-6-oxocyclohex-1-enyl)methyl acetate

: 1110689-55-8
(1S,5R,6R)-5-hydroxy-3-(hydroxymethyl)-6-((E)-1-iodoprop-1-en-2-yl)-4-oxocyclohex-2-enyl acetate

Guidance literature:: With water; scandium tris(trifluoromethanesulfonate); In methanol; at 20 ℃; for 40h; regioselective reaction;
DOI:10.1021/ja809491b

Reference yield:

: 75-47-8
iodoform

: (R,E)-2,6-dimethylhept-3-enal

: 1110689-55-8
(1S,5R,6R)-5-hydroxy-3-(hydroxymethyl)-6-((E)-1-iodoprop-1-en-2-yl)-4-oxocyclohex-2-enyl acetate

: 594-19-4
tert.-butyl lithium

: 1111232-71-3
((3S,4R,5R)-3-acetoxy-4-((S,2E,4E,7E)-6,10-dimethylundeca-2,4,7-trien-2-yl)-5-hydroxy-6-oxocyclohex-1-enyl)methyl acetate

: C₂₂H₃₂O₅

Guidance literature:: iodoform; (R,E)-2,6-dimethylhept-3-enal; With chromium dichloride; In tetrahydrofuran; at 0 ℃; for 4h;

tert.-butyl lithium; In tetrahydrofuran; at -78 ℃;

(1S,5R,6R)-5-hydroxy-3-(hydroxymethyl)-6-((E)-1-iodoprop-1-en-2-yl)-4-oxocyclohex-2-enyl acetate; Further stages;
DOI:10.1021/ja809491b

Reference yield:

: 75-47-8
iodoform

: (S,E)-2,6-dimethylhept-3-enal

: 1110689-55-8
(1S,5R,6R)-5-hydroxy-3-(hydroxymethyl)-6-((E)-1-iodoprop-1-en-2-yl)-4-oxocyclohex-2-enyl acetate

: 594-19-4
tert.-butyl lithium

: 1111232-68-8
((3S,4R,5R)-3-acetoxy-4-((R,2E,4E,7E)-6,10-dimethylundeca-2,4,7-trien-2-yl)-5-hydroxy-6-oxocyclohex-1-enyl)methyl acetate

: C₂₂H₃₂O₅

Guidance literature:: iodoform; (S,E)-2,6-dimethylhept-3-enal; With chromium dichloride; In tetrahydrofuran; at 0 ℃; for 4h;

tert.-butyl lithium; In tetrahydrofuran; at -78 ℃;

(1S,5R,6R)-5-hydroxy-3-(hydroxymethyl)-6-((E)-1-iodoprop-1-en-2-yl)-4-oxocyclohex-2-enyl acetate; Further stages;
DOI:10.1021/ja809491b