(1R,2S,5S)-2-((S)-2-Benzyloxy-1-benzyloxymethoxy-1-hydroxymethyl-ethyl)-5-vinyl-cyclohexanol

Base Information

Chemical Name:(1R,2S,5S)-2-((S)-2-Benzyloxy-1-benzyloxymethoxy-1-hydroxymethyl-ethyl)-5-vinyl-cyclohexanol
CAS No.:88670-99-9
Molecular Formula:C₂₆H₃₄O₅
Molecular Weight:426.553
Hs Code.:

Synonyms:(1R,2S,5S)-2-((S)-2-Benzyloxy-1-benzyloxymethoxy-1-hydroxymethyl-ethyl)-5-vinyl-cyclohexanol

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Chemical Property of (1R,2S,5S)-2-((S)-2-Benzyloxy-1-benzyloxymethoxy-1-hydroxymethyl-ethyl)-5-vinyl-cyclohexanol

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Technology Process of (1R,2S,5S)-2-((S)-2-Benzyloxy-1-benzyloxymethoxy-1-hydroxymethyl-ethyl)-5-vinyl-cyclohexanol

There total 7 articles about (1R,2S,5S)-2-((S)-2-Benzyloxy-1-benzyloxymethoxy-1-hydroxymethyl-ethyl)-5-vinyl-cyclohexanol 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%

: 82167-72-4
(3R,3aS,6S,7aR)-3-<(benzyloxy)methoxy>-3-<(benzyloxy)methyl>hexahydro-6-vinyl-2(3H)-benzofuranone

: 88670-99-9
(1R,2S,5S)-2-((S)-2-Benzyloxy-1-benzyloxymethoxy-1-hydroxymethyl-ethyl)-5-vinyl-cyclohexanol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃;
DOI:10.1021/jo00179a018

Reference yield:

: 82167-73-5
(4S)-7-<(benzyloxy)methoxy>-p-mentha-1,8-diene-7-carbonitrile

: 88670-99-9
(1R,2S,5S)-2-((S)-2-Benzyloxy-1-benzyloxymethoxy-1-hydroxymethyl-ethyl)-5-vinyl-cyclohexanol

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) thexylborane 2.) 30percent H₂O₂, NaOAc / 1.a.) -40 deg C 1.b.) 3 h, 23 deg C 2.) 1 h, 50 deg C

2: 40percent aqueous KOH / ethanol / 2 h / 120 °C

3: triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / -20 °C

4: Jones reagent / acetone / 0.5 h / 0 °C

5: 1.) cupric acetate monohydrate 2.) lead tetraacetate / pyridine / 1.) 0.5 h, room temperature 2a.) 1 h, 23 deg C 2b.) 2 h, 80 deg C

6: LDA / 1.) -78 deg C, 1 h 2.) -40 deg C, 2 h

7: 86 percent / LAH / tetrahydrofuran / 0 °C

With lead(IV) acetate; potassium hydroxide; lithium aluminium tetrahydride; jones reagent; thexylborane; dihydrogen peroxide; copper diacetate; sodium acetate; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; pyridine; In tetrahydrofuran; ethanol; acetone;
DOI:10.1021/jo00179a018

Reference yield:

: 88670-93-3
(1S,2S,4S)-7-<(benzyloxy)methoxy>-2,9-dihydroxy-p-methane-7-carbonitrile

: 88670-99-9
(1R,2S,5S)-2-((S)-2-Benzyloxy-1-benzyloxymethoxy-1-hydroxymethyl-ethyl)-5-vinyl-cyclohexanol

Guidance literature:: Multi-step reaction with 6 steps

1: 40percent aqueous KOH / ethanol / 2 h / 120 °C

2: triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / -20 °C

3: Jones reagent / acetone / 0.5 h / 0 °C

4: 1.) cupric acetate monohydrate 2.) lead tetraacetate / pyridine / 1.) 0.5 h, room temperature 2a.) 1 h, 23 deg C 2b.) 2 h, 80 deg C

5: LDA / 1.) -78 deg C, 1 h 2.) -40 deg C, 2 h

6: 86 percent / LAH / tetrahydrofuran / 0 °C

With lead(IV) acetate; potassium hydroxide; lithium aluminium tetrahydride; jones reagent; copper diacetate; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; pyridine; In tetrahydrofuran; ethanol; acetone;
DOI:10.1021/jo00179a018