(2R,3S,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxymethyl-3-methyl-tetrahydro-pyran-3,5-diol

Base Information

Chemical Name:(2R,3S,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxymethyl-3-methyl-tetrahydro-pyran-3,5-diol
CAS No.:154547-74-7
Molecular Formula:C₂₃H₃₂O₅Si
Molecular Weight:416.59
Hs Code.:

Synonyms:(2R,3S,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxymethyl-3-methyl-tetrahydro-pyran-3,5-diol

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Chemical Property of (2R,3S,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxymethyl-3-methyl-tetrahydro-pyran-3,5-diol

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Technology Process of (2R,3S,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxymethyl-3-methyl-tetrahydro-pyran-3,5-diol

There total 4 articles about (2R,3S,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxymethyl-3-methyl-tetrahydro-pyran-3,5-diol 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: 58.0%

: 154547-71-4
(2R,3S,4R,5R)-5-Acetoxy-6-<(tert-butyldimethylsilyl)oxy>-4-<(tert-butyldiphenylsilyl)oxy>-1,2-epoxy-4-methyl-3-hexanol

: 154547-74-7
(2R,3S,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxymethyl-3-methyl-tetrahydro-pyran-3,5-diol

: 154547-73-6
(2R,3S,4S,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-tetrahydro-pyran-3,5-diol

Guidance literature:: With sodium hydroxide; In tert-butyl alcohol; for 48h; Heating;
DOI:10.1021/jo00085a038

Reference yield:

: 154547-68-9
Acetic acid (1R,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-4-(tert-butyl-diphenyl-silanyl)-2-hydroxy-2-methyl-3-oxo-pent-4-enyl ester

: 154547-74-7
(2R,3S,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxymethyl-3-methyl-tetrahydro-pyran-3,5-diol

Guidance literature:: Multi-step reaction with 4 steps

1: DBU / CH₂Cl₂ / Ambient temperature

2: NaBH₄, CeCl₃*7H₂O / methanol

3: 85 percent / tert-BuOOH, VO(acac)2 / toluene; 2,2,4-trimethyl-pentane / 5 h / Ambient temperature

4: 10 percent / 1N NaOH / 2-methyl-propan-2-ol / 48 h / Heating

With tert.-butylhydroperoxide; sodium hydroxide; sodium tetrahydroborate; cerium(III) chloride; bis(acetylacetonate)oxovanadium; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; 2,2,4-trimethylpentane; dichloromethane; toluene; tert-butyl alcohol;
DOI:10.1021/jo00085a038

Reference yield:

: 154547-69-0
Acetic acid (1R,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-(tert-butyl-diphenyl-silanyloxy)-2-methyl-3-oxo-pent-4-enyl ester

: 154547-74-7
(2R,3S,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxymethyl-3-methyl-tetrahydro-pyran-3,5-diol

Guidance literature:: Multi-step reaction with 3 steps

1: NaBH₄, CeCl₃*7H₂O / methanol

2: 85 percent / tert-BuOOH, VO(acac)2 / toluene; 2,2,4-trimethyl-pentane / 5 h / Ambient temperature

3: 10 percent / 1N NaOH / 2-methyl-propan-2-ol / 48 h / Heating

With tert.-butylhydroperoxide; sodium hydroxide; sodium tetrahydroborate; cerium(III) chloride; bis(acetylacetonate)oxovanadium; In methanol; 2,2,4-trimethylpentane; toluene; tert-butyl alcohol;
DOI:10.1021/jo00085a038