(2R,3S)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-hexene-1,2,3-triol

Base Information

Chemical Name:(2R,3S)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-hexene-1,2,3-triol
CAS No.:160998-95-8
Molecular Formula:C₂₅H₃₄O₃Si
Molecular Weight:410.629
Hs Code.:

Synonyms:(2R,3S)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-hexene-1,2,3-triol

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Chemical Property of (2R,3S)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-hexene-1,2,3-triol

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Technology Process of (2R,3S)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-hexene-1,2,3-triol

There total 1 articles about (2R,3S)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-hexene-1,2,3-triol 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%

: 79364-35-5
(S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

: 58479-61-1
tert-butylchlorodiphenylsilane

: 160998-95-8
(2R,3S)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-hexene-1,2,3-triol

Guidance literature:: With 1H-imidazole; dmap; In N,N-dimethyl-formamide; for 24h; Ambient temperature;
DOI:10.1021/jo951444u

Reference yield:

: 160998-95-8
(2R,3S)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-hexene-1,2,3-triol

: (1S,5R,6S,7S)-6-benzoyloxymethyl-7-tert-butyldiphenylsilyloxy-2-oxabicyclo<3.3.0>octan-3-one

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) O₃, 2.) PPh₃ / 1.) methanol, -78 deg C, 2.) methanol, 12 h

2: 1.) 1.6M BuLi / 1.) THF, Et₂O, pentane, hexane, -78 deg C, 15 min, 2.) THF, Et₂O, pentane, hexane, -78 deg C; quenching with Me₃SiCl

3: 1.) H₂, quinoline, 2.) TsOH / 1.) 5percent Pd/BaSO₄ / 1.) methanol, 22 deg C, 1 bar, 2.) methanol, pH 2.5, 22 deg C, 15 h

4: pyridine / 1.) 0 deg C, 1 h, 2.) 22 deg C, 3 h

5: DMAP, pyridine / CH₂Cl₂ / 3 h / Heating

6: 810 mg / Bu₃SnH, AIBN / toluene / 2 h / Heating

With pyridine; quinoline; dmap; n-butyllithium; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; ozone; triphenylphosphine; Pd-BaSO₄; In dichloromethane; toluene;

Reference yield:

: 160998-95-8
(2R,3S)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-hexene-1,2,3-triol

: 161104-50-3
(1R,5S,6R,7S)-6-benzoyloxymethyl-7-tert-butyldiphenylsilyloxy-2-oxabicyclo<3.3.0>octan-3-one

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) O₃, 2.) PPh₃ / 1.) methanol, -78 deg C, 2.) methanol, 12 h

2: 1.) 1.6M BuLi / 1.) THF, Et₂O, pentane, hexane, -78 deg C, 15 min, 2.) THF, Et₂O, pentane, hexane, -78 deg C; quenching with Me₃SiCl

3: 1.) H₂, quinoline, 2.) TsOH / 1.) 5percent Pd/BaSO₄ / 1.) methanol, 22 deg C, 1 bar, 2.) methanol, pH 2.5, 22 deg C, 15 h

4: pyridine / 1.) 0 deg C, 1 h, 2.) 22 deg C, 3 h

5: DMAP, pyridine / CH₂Cl₂ / 3 h / Heating

6: 34 percent / Bu₃SnH, AIBN / toluene / 2 h / Heating

With pyridine; quinoline; dmap; n-butyllithium; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; ozone; triphenylphosphine; Pd-BaSO₄; In dichloromethane; toluene;