Acetic acid (3R,4S,5S,6R)-6-acetoxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-5-methyl-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Acetic acid (3R,4S,5S,6R)-6-acetoxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-5-methyl-tetrahydro-pyran-3-yl ester
CAS No.:154547-76-9
Molecular Formula:C₂₇H₃₆O₇Si
Molecular Weight:500.664
Hs Code.:

Synonyms:Acetic acid (3R,4S,5S,6R)-6-acetoxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-5-methyl-tetrahydro-pyran-3-yl ester

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Chemical Property of Acetic acid (3R,4S,5S,6R)-6-acetoxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-5-methyl-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (3R,4S,5S,6R)-6-acetoxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-5-methyl-tetrahydro-pyran-3-yl ester

There total 5 articles about Acetic acid (3R,4S,5S,6R)-6-acetoxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-5-methyl-tetrahydro-pyran-3-yl ester 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: 98.0%

: 108-24-7
acetic anhydride

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

: 154547-76-9
Acetic acid (3R,4S,5S,6R)-6-acetoxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-5-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: With pyridine; dmap; In dichloromethane; for 5h; Ambient temperature;
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

: 154547-76-9
Acetic acid (3R,4S,5S,6R)-6-acetoxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-5-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 5 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

5: 98 percent / pyridine, DMAP / CH₂Cl₂ / 5 h / Ambient temperature

With pyridine; tert.-butylhydroperoxide; dmap; 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:

: 154547-70-3
Acetic acid (1R,2R,3S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2-methyl-pent-4-enyl ester

: 154547-76-9
Acetic acid (3R,4S,5S,6R)-6-acetoxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-5-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 85 percent / tert-BuOOH, VO(acac)2 / toluene; 2,2,4-trimethyl-pentane / 5 h / Ambient temperature

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

3: 98 percent / pyridine, DMAP / CH₂Cl₂ / 5 h / Ambient temperature

With pyridine; tert.-butylhydroperoxide; dmap; sodium hydroxide; bis(acetylacetonate)oxovanadium; In 2,2,4-trimethylpentane; dichloromethane; toluene; tert-butyl alcohol;
DOI:10.1021/jo00085a038