(2R,3S,4S)-(-)-5-tert-butyldimethylsilyloxy-3,4-epoxy-2,4-dimethylpentyl benzyl ether

Base Information

Chemical Name:(2R,3S,4S)-(-)-5-tert-butyldimethylsilyloxy-3,4-epoxy-2,4-dimethylpentyl benzyl ether
CAS No.:86046-98-2
Molecular Formula:C₂₀H₃₄O₃Si
Molecular Weight:350.574
Hs Code.:

Synonyms:(2R,3S,4S)-(-)-5-tert-butyldimethylsilyloxy-3,4-epoxy-2,4-dimethylpentyl benzyl ether

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Chemical Property of (2R,3S,4S)-(-)-5-tert-butyldimethylsilyloxy-3,4-epoxy-2,4-dimethylpentyl benzyl ether

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Technology Process of (2R,3S,4S)-(-)-5-tert-butyldimethylsilyloxy-3,4-epoxy-2,4-dimethylpentyl benzyl ether

There total 9 articles about (2R,3S,4S)-(-)-5-tert-butyldimethylsilyloxy-3,4-epoxy-2,4-dimethylpentyl benzyl ether 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: 90.0%

: 80925-23-1
(2S,3S,4R)-(-)-5-benzyloxy-2,3-epoxy-2,4-dimethylpentanol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 86046-98-2
(2R,3S,4S)-(-)-5-tert-butyldimethylsilyloxy-3,4-epoxy-2,4-dimethylpentyl benzyl ether

Guidance literature:: With 1H-imidazole; at 25 ℃;
DOI:10.1016/S0040-4039(01)82028-1

Reference yield:

: 63930-46-1
(S)-3-benzyloxy-2-methylpropan-1-ol

: 86046-98-2
(2R,3S,4S)-(-)-5-tert-butyldimethylsilyloxy-3,4-epoxy-2,4-dimethylpentyl benzyl ether

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) dichloromethane, -60 deg C, 30 min, 2.) -25 deg C, 15 min

2: 1.) butyllithium,diisopropylamine, 2.) oxalic acid dihydrate, 3.) water / 1.) THF, -78 deg C, 1.25 h, 25 deg C, 2 h, 2.) reflux, 1 h, 3.) reflux, 1.5 h

3: 95 percent / sodium borohydride / ethanol / 3 h / 25 °C

4: 1.) titanium tetraisopropoxide, diethyl (+)-tartrate, 2.) tert-butyl hydroperoxide, 3.) tartaric acid / 1.) dichloromethane, -25 deg C, 10 min, 2.) -25 deg C, 3.) water, -25 deg C, 30 min, -25 deg C -> 25 deg C (1 h)

5: 90 percent / imidazole / dimethylformamide / 24 h / 25 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; diethyl (2R,3R)-tartrate; water; oxalic acid; dimethyl sulfoxide; tartaric acid; triethylamine; diisopropylamine; In ethanol; N,N-dimethyl-formamide;
DOI:10.1021/ja00353a027

Reference yield:

: 79026-61-2
(R)-3-benzyloxy-2-methylpropanal

: 86046-98-2
(2R,3S,4S)-(-)-5-tert-butyldimethylsilyloxy-3,4-epoxy-2,4-dimethylpentyl benzyl ether

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) butyllithium,diisopropylamine, 2.) oxalic acid dihydrate, 3.) water / 1.) THF, -78 deg C, 1.25 h, 25 deg C, 2 h, 2.) reflux, 1 h, 3.) reflux, 1.5 h

2: 95 percent / sodium borohydride / ethanol / 3 h / 25 °C

3: 1.) titanium tetraisopropoxide, diethyl (+)-tartrate, 2.) tert-butyl hydroperoxide, 3.) tartaric acid / 1.) dichloromethane, -25 deg C, 10 min, 2.) -25 deg C, 3.) water, -25 deg C, 30 min, -25 deg C -> 25 deg C (1 h)

4: 90 percent / imidazole / dimethylformamide / 24 h / 25 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; n-butyllithium; diethyl (2R,3R)-tartrate; water; oxalic acid; tartaric acid; diisopropylamine; In ethanol; N,N-dimethyl-formamide;
DOI:10.1021/ja00353a027