(Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-threo-hex-4-enofuranose

Base Information

• Chemical Name: (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-threo-hex-4-enofuranose
• CAS No.: 120575-50-0
• Molecular Formula: C₁₆H₂₀O₄
• Molecular Weight: 276.332

Synonyms:(Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-threo-hex-4-enofuranose

Chemical Property of (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-threo-hex-4-enofuranose

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Technology Process of (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-threo-hex-4-enofuranose

There total 4 articles about (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-threo-hex-4-enofuranose 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: 43.0%

3-O-benzyl-6-deoxy-1,2-O-isopropylidene-5-O-methanesulfonyl-β-L-idofuranose (99750-18-2) → 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose (19877-13-5) + (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-threo-hex-4-enofuranose (120575-50-0) + 3-O-benzyl-5,6-dideoxy-5-fluoro-1,2-O-isopropylidene-α-D-glucofuranose

Guidance literature:

With tetrabutyl ammonium fluoride; In N,N-dimethyl-formamide; at 120 ℃; for 18h;

DOI:10.1248/cpb.41.755

Reference yield: 23.0%

Trifluoro-methanesulfonic acid (S)-1-((3aR,5S,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester → 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose (19877-13-5) + (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-threo-hex-4-enofuranose (120575-50-0) + 3-O-benzyl-5,6-dideoxy-5-fluoro-1,2-O-isopropylidene-α-D-glucofuranose

Guidance literature:

With tris(dimethylamino)sulfonium trimethylsilyldifluoride; In dichloromethane; at 40 ℃; for 1h;

DOI:10.1246/bcsj.67.236

Reference yield: 3.0%

3-O-benzyl-6-deoxy-1,2-O-isopropylidene-5-C-methyl-β-L-ido-pentofuranose (18439-45-7) → 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose (19877-13-5) + (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-threo-hex-4-enofuranose (120575-50-0) + 3-O-benzyl-5,6-dideoxy-5-fluoro-1,2-O-isopropylidene-β-L-idofuranose + 3-O-benzyl-5,6-dideoxy-5-fluoro-1,2-O-isopropylidene-α-D-glucofuranose

Guidance literature:

With diethylamino-sulfur trifluoride; In dichloromethane; a) -10 deg C, 0.5 h, b) RT, 1 h;

DOI:10.1246/bcsj.67.236

upstream raw materials:

3-O-benzyl-6-deoxy-1,2-O-isopropylidene-5-C-methyl-β-L-ido-pentofuranose

3-O-benzyl-6-deoxy-1,2-O-isopropylidene-5-O-methanesulfonyl-β-L-idofuranose

Downstream raw materials:

C₁₈H₂₀Cl₂O₅

C₁₈H₂₂O₅

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