(2R,3R,4R)-2,3-epoxy-4-(methoxymethyl)oxy-1-{[(4'-methoxyphenyl)methyl]oxy}hexyl-6-methanesulfonate

Base Information

Chemical Name:(2R,3R,4R)-2,3-epoxy-4-(methoxymethyl)oxy-1-{[(4'-methoxyphenyl)methyl]oxy}hexyl-6-methanesulfonate
CAS No.:203248-30-0
Molecular Formula:C₁₇H₂₆O₈S
Molecular Weight:390.455
Hs Code.:

Synonyms:(2R,3R,4R)-2,3-epoxy-4-(methoxymethyl)oxy-1-{[(4'-methoxyphenyl)methyl]oxy}hexyl-6-methanesulfonate

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Chemical Property of (2R,3R,4R)-2,3-epoxy-4-(methoxymethyl)oxy-1-{[(4'-methoxyphenyl)methyl]oxy}hexyl-6-methanesulfonate

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Technology Process of (2R,3R,4R)-2,3-epoxy-4-(methoxymethyl)oxy-1-{[(4'-methoxyphenyl)methyl]oxy}hexyl-6-methanesulfonate

There total 8 articles about (2R,3R,4R)-2,3-epoxy-4-(methoxymethyl)oxy-1-{[(4'-methoxyphenyl)methyl]oxy}hexyl-6-methanesulfonate 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:

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

: 203248-30-0
(2R,3R,4R)-2,3-epoxy-4-(methoxymethyl)oxy-1-{[(4'-methoxyphenyl)methyl]oxy}hexyl-6-methanesulfonate

Guidance literature:: Multi-step reaction with 7 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

7: 3.89 g / DMAP / CH₂Cl₂ / 0.25 h / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; 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 / 7: mesylation;
DOI:10.1016/S0040-4020(00)00730-4

Reference yield:

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

: 203248-30-0
(2R,3R,4R)-2,3-epoxy-4-(methoxymethyl)oxy-1-{[(4'-methoxyphenyl)methyl]oxy}hexyl-6-methanesulfonate

Guidance literature:: Multi-step reaction with 2 steps

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

2: 3.89 g / DMAP / CH₂Cl₂ / 0.25 h / 0 °C

With dmap; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; 1: desilylation / 2: mesylation;
DOI:10.1016/S0040-4020(00)00730-4

Reference yield:

: 203248-26-4
(E)-(R)-6-(tert-butyldimethylsilyl)oxy-4-(methoxymethyl)oxy-2-hexen-1-ol

: 203248-30-0
(2R,3R,4R)-2,3-epoxy-4-(methoxymethyl)oxy-1-{[(4'-methoxyphenyl)methyl]oxy}hexyl-6-methanesulfonate

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / Ti(OPr-i)4; D-(-)-diethyl tartrate; TBHP / CH₂Cl₂ / 5 h / -20 °C

2: 95 percent / NaH / tetrahydrofuran; dimethylformamide / 1 h / 0 °C

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

4: 3.89 g / DMAP / CH₂Cl₂ / 0.25 h / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; diethyl (2S,3S)-tartrate; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Epoxidation / 2: Alkylation / 3: desilylation / 4: mesylation;
DOI:10.1016/S0040-4020(00)00730-4