Toluene-4-sulfonic acid (2R,3R,4R,5S)-2-benzyl-3,4-dihydroxy-5-triisopropylsilanyloxy-tetrahydro-furan-3-ylmethyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (2R,3R,4R,5S)-2-benzyl-3,4-dihydroxy-5-triisopropylsilanyloxy-tetrahydro-furan-3-ylmethyl ester
CAS No.:184881-62-7
Molecular Formula:C₂₈H₄₂O₇SSi
Molecular Weight:550.789
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (2R,3R,4R,5S)-2-benzyl-3,4-dihydroxy-5-triisopropylsilanyloxy-tetrahydro-furan-3-ylmethyl ester

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Chemical Property of Toluene-4-sulfonic acid (2R,3R,4R,5S)-2-benzyl-3,4-dihydroxy-5-triisopropylsilanyloxy-tetrahydro-furan-3-ylmethyl ester

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Technology Process of Toluene-4-sulfonic acid (2R,3R,4R,5S)-2-benzyl-3,4-dihydroxy-5-triisopropylsilanyloxy-tetrahydro-furan-3-ylmethyl ester

There total 7 articles about Toluene-4-sulfonic acid (2R,3R,4R,5S)-2-benzyl-3,4-dihydroxy-5-triisopropylsilanyloxy-tetrahydro-furan-3-ylmethyl 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: 55.0%

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: Toluene-4-sulfonic acid (2R,3R,4R)-2-benzyl-3,4,5-trihydroxy-tetrahydro-furan-3-ylmethyl ester

: 184881-62-7
Toluene-4-sulfonic acid (2R,3R,4R,5S)-2-benzyl-3,4-dihydroxy-5-triisopropylsilanyloxy-tetrahydro-furan-3-ylmethyl ester

: 184881-66-1
Toluene-4-sulfonic acid (2R,3R,4R,5R)-2-benzyl-3,4-dihydroxy-5-triisopropylsilanyloxy-tetrahydro-furan-3-ylmethyl ester

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane;
DOI:10.1246/cl.1996.931

Reference yield:

: 63522-23-6
3-desoxy-1,2-O-isopropylidene-3-C-methylidene-α-D-erythro-pentodialdo-1,4-furanose

: 184881-62-7
Toluene-4-sulfonic acid (2R,3R,4R,5S)-2-benzyl-3,4-dihydroxy-5-triisopropylsilanyloxy-tetrahydro-furan-3-ylmethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 82 percent / diethyl ether

2: 1.) NaH, imidazole, CS₂, MeI, 2.) n-Bu₃SnH, AIBN / 1.) THF, 2.) toluene

3: 94 percent / OsO₄, NMO / H₂O; acetone

4: 100 percent / DMAP, pyridine

5: 85 percent / 4 M aq. HCl / tetrahydrofuran

6: 44 percent / 2,6-lutidine / CH₂Cl₂

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; carbon disulfide; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; methyl iodide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone;
DOI:10.1246/cl.1996.931

Reference yield:

: 100-58-3
phenylmagnesium bromide

: 184881-62-7
Toluene-4-sulfonic acid (2R,3R,4R,5S)-2-benzyl-3,4-dihydroxy-5-triisopropylsilanyloxy-tetrahydro-furan-3-ylmethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 82 percent / diethyl ether

2: 1.) NaH, imidazole, CS₂, MeI, 2.) n-Bu₃SnH, AIBN / 1.) THF, 2.) toluene

3: 94 percent / OsO₄, NMO / H₂O; acetone

4: 100 percent / DMAP, pyridine

5: 85 percent / 4 M aq. HCl / tetrahydrofuran

6: 44 percent / 2,6-lutidine / CH₂Cl₂

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; carbon disulfide; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; methyl iodide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone;
DOI:10.1246/cl.1996.931