{(4R,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol

Base Information

• Chemical Name: {(4R,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol
• CAS No.: 214678-52-1
• Molecular Formula: C₁₉H₃₂O₄Si
• Molecular Weight: 352.546

Synonyms:{(4R,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol

Chemical Property of {(4R,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol

Chemical Property:

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Technology Process of {(4R,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol

There total 13 articles about {(4R,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol 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: 100.0%

ethyl (4S,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate (187931-99-3) → {(4R,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol (214678-52-1)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 0.0833333h;

DOI:10.1016/S0040-4039(98)01562-7

Reference yield: 91.0%

(4S)-4-t-butyldimethylsilyloxy-4-phenyl-2S,3S-O-isopropylidene-butyl benzyl ether (338385-68-5) → {(4R,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol (214678-52-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 45 ℃; for 6h; under 760 Torr;

DOI:10.1016/S0040-4020(01)00050-3

Reference yield: 82.0%

(tert-butyl)[(R)-[(4S,5R)-5-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)-2,2-dimethyl-1,3-dioxolan-4-yl](phenyl)methoxy]dimethylsilane → {(4R,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol (214678-52-1)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1002/hlca.201400237

upstream raw materials:

ethyl (4S,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate

(4S)-4-t-butyldimethylsilyloxy-4-phenyl-2S,3S-O-isopropylidene-butyl benzyl ether

4-O-benzyl-2,3-O-isopropylidene-D-threose

tert-butyldimethylsilyl chloride

Downstream raw materials:

(2R,3S,4R)-1-(t-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-4-phenyl-1-trifluoromethanesulfonyloxybutane

(2S,3S)-2-[(1R,2R)-1,2-dihydroxy-2-phenylethyl]-6-oxo-3,6-dihydro-2H-pyran-3-yl (2E)-3-phenylprop-2-enoate

3-Benzenesulfonyl-4-{(4R,5S)-5-[(R)-(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-butyric acid methyl ester

(R)-4-Benzenesulfonyl-6-((1R,2R)-1,2-dihydroxy-2-phenyl-ethyl)-tetrahydro-pyran-2-one

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