{(2R,3R)-3-[(R)-2-((1S,3R,4R)-3,4-Bis-benzyloxy-cyclohexyl)-1-methyl-ethyl]-oxiranyl}-methanol

Base Information

Chemical Name:{(2R,3R)-3-[(R)-2-((1S,3R,4R)-3,4-Bis-benzyloxy-cyclohexyl)-1-methyl-ethyl]-oxiranyl}-methanol
CAS No.:725268-49-5
Molecular Formula:C₂₆H₃₄O₄
Molecular Weight:410.554
Hs Code.:

Synonyms:{(2R,3R)-3-[(R)-2-((1S,3R,4R)-3,4-Bis-benzyloxy-cyclohexyl)-1-methyl-ethyl]-oxiranyl}-methanol

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Chemical Property of {(2R,3R)-3-[(R)-2-((1S,3R,4R)-3,4-Bis-benzyloxy-cyclohexyl)-1-methyl-ethyl]-oxiranyl}-methanol

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Technology Process of {(2R,3R)-3-[(R)-2-((1S,3R,4R)-3,4-Bis-benzyloxy-cyclohexyl)-1-methyl-ethyl]-oxiranyl}-methanol

There total 11 articles about {(2R,3R)-3-[(R)-2-((1S,3R,4R)-3,4-Bis-benzyloxy-cyclohexyl)-1-methyl-ethyl]-oxiranyl}-methanol 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: 99.0%

: 725268-48-4
(E)-(R)-5-((1S,3R,4R)-3,4-Bis-benzyloxy-cyclohexyl)-4-methyl-pent-2-en-1-ol

: 725268-49-5
{(2R,3R)-3-[(R)-2-((1S,3R,4R)-3,4-Bis-benzyloxy-cyclohexyl)-1-methyl-ethyl]-oxiranyl}-methanol

Guidance literature:: With titanium(IV) isopropylate; 4 A molecular sieve; (-)-diethyl tartrate; tert.-butylhydroperoxide; In decane; dichloromethane; at -20 ℃; for 4h;
DOI:10.1016/j.tet.2004.04.072

Reference yield:

: 2-((4R,5R)-4,5-Bis-benzyloxy-cyclohex-2-enyl)-ethanol

: 725268-49-5
{(2R,3R)-3-[(R)-2-((1S,3R,4R)-3,4-Bis-benzyloxy-cyclohexyl)-1-methyl-ethyl]-oxiranyl}-methanol

Guidance literature:: Multi-step reaction with 11 steps

1.1: 80 percent / p-TsNHNH₂; aq. NaOAc / 1,2-dimethoxy-ethane / 5 h / 95 °C

2.1: 92 percent / EtN₃; DMAP / CH₂Cl₂ / 4 h / 20 °C

3.1: 91 percent / dimethylsulfoxide / 4 h / 60 °C

4.1: 100 percent / KOH / ethanol; H₂O / Heating

5.1: Et₃N; pivaloyl chloride / tetrahydrofuran / 1.5 h / -78 - 0 °C

5.2: 92 percent / LiCl / tetrahydrofuran / 20 °C

6.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

6.2: 94 percent / tetrahydrofuran / 6 h / -78 °C

7.1: 91 percent / LiAlH₄ / tetrahydrofuran / 0 °C

8.1: (COCl)2; DMSO / CH₂Cl₂ / 0.25 h / -78 °C

9.1: CH₂Cl₂ / 20 °C

10.1: 872.1 mg / DIBALH / CH₂Cl₂; hexane / 1 h / -78 °C

11.1: 99 percent / molecular sieves 4 Angstroem; (-)-diethyl tartrate; Ti(O-iPr)4 / t-butyl hydroperoxide / CH₂Cl₂; decane / 4 h / -20 °C

With titanium(IV) isopropylate; dmap; potassium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; 4 A molecular sieve; sodium acetate; sodium hexamethyldisilazane; pivaloyl chloride; diisobutylaluminium hydride; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; toluene-4-sulfonic acid hydrazide; ethyl azide; tert.-butylhydroperoxide; In tetrahydrofuran; 1,2-dimethoxyethane; decane; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; 9.1: Wittig reaction / 11.1: Sharpless asymmetric epoxidation;
DOI:10.1016/j.tet.2004.04.072

Reference yield:

: (R)-3-((1S,3R,4R)-3,4-Bis-benzyloxy-cyclohexyl)-2-methyl-propionaldehyde

: 725268-49-5
{(2R,3R)-3-[(R)-2-((1S,3R,4R)-3,4-Bis-benzyloxy-cyclohexyl)-1-methyl-ethyl]-oxiranyl}-methanol

Guidance literature:: Multi-step reaction with 3 steps

1: CH₂Cl₂ / 20 °C

2: 872.1 mg / DIBALH / CH₂Cl₂; hexane / 1 h / -78 °C

3: 99 percent / molecular sieves 4 Angstroem; (-)-diethyl tartrate; Ti(O-iPr)4 / t-butyl hydroperoxide / CH₂Cl₂; decane / 4 h / -20 °C

With titanium(IV) isopropylate; 4 A molecular sieve; diisobutylaluminium hydride; (-)-diethyl tartrate; tert.-butylhydroperoxide; In decane; hexane; dichloromethane; 1: Wittig reaction / 3: Sharpless asymmetric epoxidation;
DOI:10.1016/j.tet.2004.04.072