(R)-3-[(2R,3R)-3-(4-Methoxy-benzyloxymethyl)-oxiranyl]-3-methoxymethoxy-propan-1-ol

Base Information

Chemical Name:(R)-3-[(2R,3R)-3-(4-Methoxy-benzyloxymethyl)-oxiranyl]-3-methoxymethoxy-propan-1-ol
CAS No.:313218-76-7
Molecular Formula:C₁₆H₂₄O₆
Molecular Weight:312.363
Hs Code.:

Synonyms:(R)-3-[(2R,3R)-3-(4-Methoxy-benzyloxymethyl)-oxiranyl]-3-methoxymethoxy-propan-1-ol

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Chemical Property of (R)-3-[(2R,3R)-3-(4-Methoxy-benzyloxymethyl)-oxiranyl]-3-methoxymethoxy-propan-1-ol

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Technology Process of (R)-3-[(2R,3R)-3-(4-Methoxy-benzyloxymethyl)-oxiranyl]-3-methoxymethoxy-propan-1-ol

There total 9 articles about (R)-3-[(2R,3R)-3-(4-Methoxy-benzyloxymethyl)-oxiranyl]-3-methoxymethoxy-propan-1-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:

: 203248-28-6
(2R,3R,4R)-6-(tert-butyldimethylsilyl)oxy-2,3-epoxy-4-(methoxymethyl)oxy-1-{[(4'-methoxyphenyl)methyl]oxy}hexane

: 313218-76-7
(R)-3-[(2R,3R)-3-(4-Methoxy-benzyloxymethyl)-oxiranyl]-3-methoxymethoxy-propan-1-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; Ambient temperature;
DOI:10.1016/S0040-4039(97)10660-8

Reference yield:

: 203248-24-2
(R)-4-(tert-butyldimethylsilyl)oxy-2-(methoxymethyl)oxybutan-1-ol

: 313218-76-7
(R)-3-[(2R,3R)-3-(4-Methoxy-benzyloxymethyl)-oxiranyl]-3-methoxymethoxy-propan-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2: tBuOK / tetrahydrofuran / 0.5 h / -42 °C

3: 12.7 g / DIBAL-H / toluene; hexane / 0.5 h / -78 °C

4: 89 percent / Ti(OPr-i)4; D-(-)-diethyl tartrate; TBHP / CH₂Cl₂ / 5 h / -20 °C

5: 95 percent / NaH / tetrahydrofuran; dimethylformamide / 1 h / 0 °C

6: TBAF / tetrahydrofuran / 1 h / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; diethyl (2S,3S)-tartrate; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Oxidation / 2: Horner-Emmons reaction / 3: Reduction / 4: Epoxidation / 5: Alkylation / 6: desilylation;
DOI:10.1016/S0040-4020(00)00730-4

Reference yield:

: 313218-75-6
(R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methoxymethoxy-butyraldehyde

: 313218-76-7
(R)-3-[(2R,3R)-3-(4-Methoxy-benzyloxymethyl)-oxiranyl]-3-methoxymethoxy-propan-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1: tBuOK / tetrahydrofuran / 0.5 h / -42 °C

2: 12.7 g / DIBAL-H / toluene; hexane / 0.5 h / -78 °C

3: 89 percent / Ti(OPr-i)4; D-(-)-diethyl tartrate; TBHP / CH₂Cl₂ / 5 h / -20 °C

4: 95 percent / NaH / tetrahydrofuran; dimethylformamide / 1 h / 0 °C

5: TBAF / tetrahydrofuran / 1 h / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Horner-Emmons reaction / 2: Reduction / 3: Epoxidation / 4: Alkylation / 5: desilylation;
DOI:10.1016/S0040-4020(00)00730-4