6-C-phenyl-3,6-dideoxy-5-O-(p-tolylsulfonyl)-1,2-O-isopropylidene-α-D-allofuranose

Base Information

• Chemical Name: 6-C-phenyl-3,6-dideoxy-5-O-(p-tolylsulfonyl)-1,2-O-isopropylidene-α-D-allofuranose
• CAS No.: 131013-18-8
• Molecular Formula: C₂₂H₂₆O₆S
• Molecular Weight: 418.511

Synonyms:6-C-phenyl-3,6-dideoxy-5-O-(p-tolylsulfonyl)-1,2-O-isopropylidene-α-D-allofuranose

Chemical Property of 6-C-phenyl-3,6-dideoxy-5-O-(p-tolylsulfonyl)-1,2-O-isopropylidene-α-D-allofuranose

Chemical Property:

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Technology Process of 6-C-phenyl-3,6-dideoxy-5-O-(p-tolylsulfonyl)-1,2-O-isopropylidene-α-D-allofuranose

There total 3 articles about 6-C-phenyl-3,6-dideoxy-5-O-(p-tolylsulfonyl)-1,2-O-isopropylidene-α-D-allofuranose 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: 95.0%

6-C-phenyl-3,6-dideoxy-1,2-O-isopropylidene-α-D-allofuranose (131013-17-7) + p-toluenesulfonyl chloride (98-59-9) → 6-C-phenyl-3,6-dideoxy-5-O-(p-tolylsulfonyl)-1,2-O-isopropylidene-α-D-allofuranose (131013-18-8)

Guidance literature:

With pyridine; at 45 ℃; for 24h;

DOI:10.1021/jo00003a040

Reference yield:

(3aR,5S,6aR)-2,2-dimethyl-5-[(2R)-oxiran-2-yl]-3a,5,6,6a-tetrahydrofuro[2,3-d] [1,3]dioxole (2457-93-4) → 6-C-phenyl-3,6-dideoxy-5-O-(p-tolylsulfonyl)-1,2-O-isopropylidene-α-D-allofuranose (131013-18-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / CuI / tetrahydrofuran / a) 1 h at -50 deg C and 30 min at -30 deg C

2: 95 percent / pyridine / 24 h / 45 °C

With pyridine; copper(l) iodide; In tetrahydrofuran;

DOI:10.1021/jo00003a040

Reference yield:

phenylmagnesium chloride → 6-C-phenyl-3,6-dideoxy-5-O-(p-tolylsulfonyl)-1,2-O-isopropylidene-α-D-allofuranose (131013-18-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / CuI / tetrahydrofuran / a) 1 h at -50 deg C and 30 min at -30 deg C

2: 95 percent / pyridine / 24 h / 45 °C

With pyridine; copper(l) iodide; In tetrahydrofuran;

DOI:10.1021/jo00003a040

upstream raw materials:

6-C-phenyl-3,6-dideoxy-1,2-O-isopropylidene-α-D-allofuranose

p-toluenesulfonyl chloride

(3aR,5S,6aR)-2,2-dimethyl-5-[(2R)-oxiran-2-yl]-3a,5,6,6a-tetrahydrofuro[2,3-d] [1,3]dioxole

Downstream raw materials:

(3aR,5S,6aR)-2,2-Dimethyl-5-((E)-styryl)-tetrahydro-furo[2,3-d][1,3]dioxole

6-C-phenyl-5-azido-3,5,6-trideoxy-1,2-O-isopropylidene-β-L-talofuranose

methyl 6-C-phenyl-5-azido-3,5,6-trideoxy-2-O-<(trifluoromethyl)sulfonyl>-β-L-talofuranoside

methyl 6-C-phenyl-5-azido-3,5,6-trideoxy-2-O-<(trifluoromethyl)sulfonyl>-α-L-talofuranoside

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