(1S,2S,3S,4R)-1-((benzyloxy)methyl)-3-methyl-3-(4-methylpent-3-en-1-yl)-2-vinylcyclohexane-1,4-diol

Base Information

Chemical Name:(1S,2S,3S,4R)-1-((benzyloxy)methyl)-3-methyl-3-(4-methylpent-3-en-1-yl)-2-vinylcyclohexane-1,4-diol
CAS No.:1422278-63-4
Molecular Formula:C₂₃H₃₄O₃
Molecular Weight:358.521
Hs Code.:

Synonyms:(1S,2S,3S,4R)-1-((benzyloxy)methyl)-3-methyl-3-(4-methylpent-3-en-1-yl)-2-vinylcyclohexane-1,4-diol

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Chemical Property of (1S,2S,3S,4R)-1-((benzyloxy)methyl)-3-methyl-3-(4-methylpent-3-en-1-yl)-2-vinylcyclohexane-1,4-diol

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Technology Process of (1S,2S,3S,4R)-1-((benzyloxy)methyl)-3-methyl-3-(4-methylpent-3-en-1-yl)-2-vinylcyclohexane-1,4-diol

There total 4 articles about (1S,2S,3S,4R)-1-((benzyloxy)methyl)-3-methyl-3-(4-methylpent-3-en-1-yl)-2-vinylcyclohexane-1,4-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: 60.0%

: 19945-61-0
(E)-4,8-dimethylnona-1,3,7-triene

: 226253-68-5
5-(benzyloxy)-4-oxopentanal

: 1422278-63-4
(1S,2S,3S,4R)-1-((benzyloxy)methyl)-3-methyl-3-(4-methylpent-3-en-1-yl)-2-vinylcyclohexane-1,4-diol

Guidance literature:: (E)-4,8-dimethylnona-1,3,7-triene; With [Pt(1,5-diphenylpenta-1,4-dien-3-one)3]; (3aR,8aR)-4,4,8,8-tetrakis(3,5-diisopropylphenyl)-2,2-dimethyl-6-phenyltetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine; bis(pinacol)diborane; In toluene; at 60 ℃; for 12h; Inert atmosphere;

5-(benzyloxy)-4-oxopentanal; In toluene; at 60 ℃; for 24h; enantioselective reaction; Inert atmosphere;
DOI:10.1021/ja400506j

Reference yield:

: 1257867-39-2
1-(benzyloxy)hex-5-en-2-one

: 1422278-63-4
(1S,2S,3S,4R)-1-((benzyloxy)methyl)-3-methyl-3-(4-methylpent-3-en-1-yl)-2-vinylcyclohexane-1,4-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: ozone / dichloromethane / -78 °C

1.2: -78 - 20 °C / Inert atmosphere

2.1: bis(pinacol)diborane; [Pt(1,5-diphenylpenta-1,4-dien-3-one)3]; (3aR,8aR)-4,4,8,8-tetrakis(3,5-diisopropylphenyl)-2,2-dimethyl-6-phenyltetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine / toluene / 12 h / 60 °C / Inert atmosphere

2.2: 24 h / 60 °C / Inert atmosphere

With [Pt(1,5-diphenylpenta-1,4-dien-3-one)3]; (3aR,8aR)-4,4,8,8-tetrakis(3,5-diisopropylphenyl)-2,2-dimethyl-6-phenyltetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine; ozone; bis(pinacol)diborane; In dichloromethane; toluene;
DOI:10.1021/ja400506j

Reference yield:

: 60656-87-3
benzyloxyacetoaldehyde

: 1422278-63-4
(1S,2S,3S,4R)-1-((benzyloxy)methyl)-3-methyl-3-(4-methylpent-3-en-1-yl)-2-vinylcyclohexane-1,4-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: magnesium; iodine / tetrahydrofuran / 65 °C / Inert atmosphere

1.2: 2 h / 0 °C / Inert atmosphere

1.3: Inert atmosphere

2.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane; acetonitrile / 20 °C / Molecular sieve

3.1: ozone / dichloromethane / -78 °C

3.2: -78 - 20 °C / Inert atmosphere

4.1: bis(pinacol)diborane; [Pt(1,5-diphenylpenta-1,4-dien-3-one)3]; (3aR,8aR)-4,4,8,8-tetrakis(3,5-diisopropylphenyl)-2,2-dimethyl-6-phenyltetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine / toluene / 12 h / 60 °C / Inert atmosphere

4.2: 24 h / 60 °C / Inert atmosphere

With tetrapropylammonium perruthennate; [Pt(1,5-diphenylpenta-1,4-dien-3-one)3]; (3aR,8aR)-4,4,8,8-tetrakis(3,5-diisopropylphenyl)-2,2-dimethyl-6-phenyltetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine; iodine; ozone; magnesium; 4-methylmorpholine N-oxide; bis(pinacol)diborane; In tetrahydrofuran; dichloromethane; toluene; acetonitrile;
DOI:10.1021/ja400506j