6-Desoxy-1,2-O-isopropyliden-3-O-(4-methylphenylsulfonyl)-α-D-glucofuranose

Base Information

• Chemical Name: 6-Desoxy-1,2-O-isopropyliden-3-O-(4-methylphenylsulfonyl)-α-D-glucofuranose
• CAS No.: 78785-02-1
• Molecular Formula: C₁₆H₂₂O₇S
• Molecular Weight: 358.412
• Mol file: 78785-02-1.mol

Synonyms:6-Desoxy-1,2-O-isopropyliden-3-O-(4-methylphenylsulfonyl)-α-D-glucofuranose

Chemical Property of 6-Desoxy-1,2-O-isopropyliden-3-O-(4-methylphenylsulfonyl)-α-D-glucofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-Desoxy-1,2-O-isopropyliden-3-O-(4-methylphenylsulfonyl)-α-D-glucofuranose

There total 4 articles about 6-Desoxy-1,2-O-isopropyliden-3-O-(4-methylphenylsulfonyl)-α-D-glucofuranose 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: 90.0%

1,2-O-Isopropyliden-3,6-bis-O-(4-methylphenylsulfonyl)-α-D-glucofuranose (16848-25-2) → 6-Desoxy-1,2-O-isopropyliden-3-O-(4-methylphenylsulfonyl)-α-D-glucofuranose (78785-02-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; Heating;

DOI:10.1002/cber.19811140605

Reference yield: 53.5%

5β-vinyl-4β-tosyl-2α,3α-O-isopropylidene tetrahydrofuran (43138-33-6) → 5-deoxy-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-α-D-xylo-hexofuranose (62102-11-8) + 6-Desoxy-1,2-O-isopropyliden-3-O-(4-methylphenylsulfonyl)-α-D-glucofuranose (78785-02-1) + 1,2-O-isopropylidene-3-O-tosyl-5,6-dideoxy-α-D-glucofuranose + 1,2-O-isopropylidene-3-O-tosyl-6-deoxy-α-D-idofuranose

Guidance literature:

5β-vinyl-4β-tosyl-2α,3α-O-isopropylidene tetrahydrofuran; With dimethylsulfide borane complex; In tetrahydrofuran; at 20 ℃; for 2h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; methanol; at 20 ℃; for 2h;

DOI:10.1016/S0957-4166(00)00136-1

Reference yield:

(3aR,5R,6S,6aR)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate (2946-01-2) → 6-Desoxy-1,2-O-isopropyliden-3-O-(4-methylphenylsulfonyl)-α-D-glucofuranose (78785-02-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: p-toluenesulfonic acid monohydrate / 24 h / 20 °C

2.1: acetic anhydride / 4 h / Heating

3.1: BH₃*SMe₂ / tetrahydrofuran / 2 h / 20 °C

3.2: 9.7 percent / NaOH; aq. H₂O₂ / methanol; tetrahydrofuran / 2 h / 20 °C

With dimethylsulfide borane complex; acetic anhydride; toluene-4-sulfonic acid; In tetrahydrofuran; 1.1: Cycloaddition / 2.1: Dehydration / 3.1: Reduction / 3.2: Hydrolysis;

DOI:10.1016/S0957-4166(00)00136-1

upstream raw materials:

1,2-O-Isopropyliden-3,6-bis-O-(4-methylphenylsulfonyl)-α-D-glucofuranose

5β-vinyl-4β-tosyl-2α,3α-O-isopropylidene tetrahydrofuran

(3aR,5R,6S,6aR)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate

3-p-toluenesulphonate of 1,2-O-isopropylidene-5,6-O-methoxymethylidene-α-D-glucofuranose

Downstream raw materials:

Methyl-6-O-benzyl-3,5-didesoxy-5-C-methyl-L-lyxo-hexofuranosid

Toluene-4-sulfonic acid (2R,3R,4R)-4,5-dihydroxy-2-((R)-2-hydroxy-1-methyl-ethyl)-tetrahydro-furan-3-yl ester

(3aR,5R,6S,6aR)-2,2-dimethyl-5-(prop-1-en-2-yl)tetrahydrofuro-[2,3-d][1,3]dioxol-6-yl4-methylbenzenesulfonate

Methyl-6-O-benzyl-5-desoxy-5-C-methyl-3-O-(4-methylphenylsulfonyl)-L-idofuranosid