(2S,3S,4S,5R)-1,2-O-isopropylidine-3,6-anhydro-4-O-benzyl-5-O-methane-sulfonyl-D-galactitol

Base Information

Chemical Name:(2S,3S,4S,5R)-1,2-O-isopropylidine-3,6-anhydro-4-O-benzyl-5-O-methane-sulfonyl-D-galactitol
CAS No.:936946-80-4
Molecular Formula:C₁₇H₂₄O₇S
Molecular Weight:372.439
Hs Code.:

Synonyms:(2S,3S,4S,5R)-1,2-O-isopropylidine-3,6-anhydro-4-O-benzyl-5-O-methane-sulfonyl-D-galactitol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3S,4S,5R)-1,2-O-isopropylidine-3,6-anhydro-4-O-benzyl-5-O-methane-sulfonyl-D-galactitol

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Technology Process of (2S,3S,4S,5R)-1,2-O-isopropylidine-3,6-anhydro-4-O-benzyl-5-O-methane-sulfonyl-D-galactitol

There total 5 articles about (2S,3S,4S,5R)-1,2-O-isopropylidine-3,6-anhydro-4-O-benzyl-5-O-methane-sulfonyl-D-galactitol 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: 85.0%

: 929202-56-2
(2S,3S,4S,5R)-1,2-O-isopropylidene-3,6-anhydro-4-O-benzyl-D-galactitol

: 124-63-0
methanesulfonyl chloride

: 936946-80-4
(2S,3S,4S,5R)-1,2-O-isopropylidine-3,6-anhydro-4-O-benzyl-5-O-methane-sulfonyl-D-galactitol

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 1.5h;
DOI:10.1002/ejoc.200801226

Reference yield:

: 80040-79-5
3,4,6-tri-O-benzyl-D-galactal

: 936946-80-4
(2S,3S,4S,5R)-1,2-O-isopropylidine-3,6-anhydro-4-O-benzyl-5-O-methane-sulfonyl-D-galactitol

Guidance literature:: Multi-step reaction with 5 steps

1: aq. H₂SO₄ / HgSO₄ / dioxane / 8 h / 0 - 20 °C

2: NaBH₄; CeCl₃*7H₂O / ethanol / 3 h / 0 - 20 °C

3: L-(+)-diethyl tartrate; t-BuOOH / Ti(O-i-Pr)4 / CH₂Cl₂ / 2.5 h / -25 - 0 °C

4: citric acid / 2 h

5: triethylamine / CH₂Cl₂ / 1.5 h / 0 - 20 °C

With tert.-butylhydroperoxide; sodium tetrahydroborate; cerium(III) chloride; diethyl (2R,3R)-tartrate; sulfuric acid; triethylamine; citric acid; titanium(IV) isopropylate; mercury(II) sulfate; In 1,4-dioxane; ethanol; dichloromethane; 1: Perlin hydrolysis / 3: Sharpless asymmetric epoxidation;
DOI:10.1016/j.tetasy.2007.02.021

Reference yield:

: 137410-20-9
(2E)-4,6-di-O-benzyl-2,3-dideoxy-aldehydo-D-threo-hex-2-enose

: 936946-80-4
(2S,3S,4S,5R)-1,2-O-isopropylidine-3,6-anhydro-4-O-benzyl-5-O-methane-sulfonyl-D-galactitol

Guidance literature:: Multi-step reaction with 4 steps

1: NaBH₄; CeCl₃*7H₂O / ethanol / 3 h / 0 - 20 °C

2: L-(+)-diethyl tartrate; t-BuOOH / Ti(O-i-Pr)4 / CH₂Cl₂ / 2.5 h / -25 - 0 °C

3: citric acid / 2 h

4: triethylamine / CH₂Cl₂ / 1.5 h / 0 - 20 °C

With tert.-butylhydroperoxide; sodium tetrahydroborate; cerium(III) chloride; diethyl (2R,3R)-tartrate; triethylamine; citric acid; titanium(IV) isopropylate; In ethanol; dichloromethane; 2: Sharpless asymmetric epoxidation;
DOI:10.1016/j.tetasy.2007.02.021