3-O-Benzyl-5-deoxy-1,2-O-isopropylidene-6-O-tosyl-α-D-xylo-hexofuranose

Base Information

• Chemical Name: 3-O-Benzyl-5-deoxy-1,2-O-isopropylidene-6-O-tosyl-α-D-xylo-hexofuranose
• CAS No.: 360562-22-7
• Molecular Formula: C₂₃H₂₈O₇S
• Molecular Weight: 448.537
• Mol file: 360562-22-7.mol

Synonyms:3-O-Benzyl-5-deoxy-1,2-O-isopropylidene-6-O-tosyl-α-D-xylo-hexofuranose

Chemical Property of 3-O-Benzyl-5-deoxy-1,2-O-isopropylidene-6-O-tosyl-α-D-xylo-hexofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-Benzyl-5-deoxy-1,2-O-isopropylidene-6-O-tosyl-α-D-xylo-hexofuranose

There total 8 articles about 3-O-Benzyl-5-deoxy-1,2-O-isopropylidene-6-O-tosyl-α-D-xylo-hexofuranose 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: 92.0%

2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethanol (57575-19-6,81686-55-7) + p-toluenesulfonyl chloride (98-59-9) → 3-O-Benzyl-5-deoxy-1,2-O-isopropylidene-6-O-tosyl-α-D-xylo-hexofuranose (360562-22-7)

Guidance literature:

With pyridine; dmap; at 20 ℃;

DOI:10.1135/cccc20010785

Reference yield:

6-O-Benzoyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose (37776-15-1) → 3-O-Benzyl-5-deoxy-1,2-O-isopropylidene-6-O-tosyl-α-D-xylo-hexofuranose (360562-22-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaH / dimethylformamide / 0.5 h / 0 °C

1.2: 91 percent / dimethylformamide / 1 h / 0 - 20 °C

2.1: Bu₃SnH; AIBN / toluene / 0.5 h / Heating

3.1: 9.85 g / NaOMe / methanol

4.1: 92 percent / DMAP; pyridine / 20 °C

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium methylate; sodium hydride; In methanol; N,N-dimethyl-formamide; toluene;

DOI:10.1135/cccc20010785

Reference yield:

Benzoic acid 2-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester → 3-O-Benzyl-5-deoxy-1,2-O-isopropylidene-6-O-tosyl-α-D-xylo-hexofuranose (360562-22-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 9.85 g / NaOMe / methanol

2: 92 percent / DMAP; pyridine / 20 °C

With pyridine; dmap; sodium methylate; In methanol;

DOI:10.1135/cccc20010785

upstream raw materials:

2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethanol

p-toluenesulfonyl chloride

6-O-Benzoyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose

6-O-Benzoyl-3-O-benzyl-1,2-O-isopropylidene-5-O-[(methylsulfanyl)thiocarbonyl]-α-D-glucofuranose

Downstream raw materials:

3-O-Benzyl-5-deoxy-1,2-O-isopropylidene-6-iodo-α-D-xylo-hexofuranose

Diethyl (3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-6-yl)malonate