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

Base Information

Chemical Name:(2R,3R,4R)-6-(tert-butyldimethylsilyl)oxy-2,3-epoxy-4-(methoxymethyl)oxy-1-{[(4'-methoxyphenyl)methyl]oxy}hexane
CAS No.:203248-28-6
Molecular Formula:C₂₂H₃₈O₆Si
Molecular Weight:426.626
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

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

There total 9 articles about (2R,3R,4R)-6-(tert-butyldimethylsilyl)oxy-2,3-epoxy-4-(methoxymethyl)oxy-1-{[(4'-methoxyphenyl)methyl]oxy}hexane 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%

: 2746-25-0
p-Methoxybenzyl bromide

: 203248-41-3
{(2R,3R)-3-[(R)-3-(tert-Butyl-dimethyl-silanyloxy)-1-methoxymethoxy-propyl]-oxiranyl}-methanol

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

Guidance literature:: With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 ℃; for 1h;
DOI:10.1016/S0040-4020(00)00730-4

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 5 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

With titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; diethyl (2S,3S)-tartrate; potassium tert-butylate; 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;
DOI:10.1016/S0040-4020(00)00730-4

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 4 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

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