(2R,4S,5R)-5-Methyl-4-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-ol

Base Information

Chemical Name:(2R,4S,5R)-5-Methyl-4-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-ol
CAS No.:131311-01-8
Molecular Formula:C₁₇H₂₂O₄
Molecular Weight:290.359
Hs Code.:

Synonyms:(2R,4S,5R)-5-Methyl-4-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-ol

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Chemical Property of (2R,4S,5R)-5-Methyl-4-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-ol

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Technology Process of (2R,4S,5R)-5-Methyl-4-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-ol

There total 16 articles about (2R,4S,5R)-5-Methyl-4-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-ol 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: 95.0%

: 131311-00-7
Trimethyl-[(2R,4S,5R)-5-methyl-4-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-yloxy]-silane

: 131311-01-8
(2R,4S,5R)-5-Methyl-4-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 0.333333h;
DOI:10.1016/S0040-4020(01)85579-4

Reference yield:

: C₁₆H₂₀O₅

: 1779-49-3
Methyltriphenylphosphonium bromide

: 131311-01-8
(2R,4S,5R)-5-Methyl-4-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-ol

Guidance literature:: Methyltriphenylphosphonium bromide; With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 0.666667h; Inert atmosphere;

C₁₆H₂₀O₅; In tetrahydrofuran; at 0 ℃; for 0.7h; Inert atmosphere;
DOI:10.1055/s-0033-1338503

Reference yield:

: 22900-10-3,35536-75-5,36792-85-5,113890-34-9,113890-37-2,133813-23-7
2-deoxy-D-ribose

: 131311-01-8
(2R,4S,5R)-5-Methyl-4-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-ol

Guidance literature:: Multi-step reaction with 10 steps

1: 97 percent / tetrahydrofuran / 3 h / Heating

2: 96 percent / camphorsulfonic acid / CH₂Cl₂ / 12 h / 25 °C

3: 89 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -78 °C

4: 84 percent / hexane; CH₂Cl₂ / 2 h / -20 °C

5: 100 percent / CH₂Cl₂ / 0.25 h / 25 °C

6: 96 percent / DIBAL / CH₂Cl₂ / 0.25 h / -78 °C

7: 1.) diethyl-D-tartrate, titanium(IV) isopropoxide, 2.) tert-butylhydroperoxide / 1.) CH₂Cl₂, -25 deg C, 30 min, 2.) 2,2,4-trimethylpentane, -20 deg C, 14 h

8: 93 percent / triethylamine, SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 2 h / 0 °C

9: 88 percent / NaN(SiMe₃)2 / tetrahydrofuran / 0.58 h / 0 °C

10: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.33 h / 25 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide;
DOI:10.1016/S0040-4020(01)85579-4