3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-3-C-methyl-α-D-ribo-hex-5-enofuranose

Base Information

• Chemical Name: 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-3-C-methyl-α-D-ribo-hex-5-enofuranose
• CAS No.: 98003-98-6
• Molecular Formula: C₁₇H₂₂O₄
• Molecular Weight: 290.359

Synonyms:3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-3-C-methyl-α-D-ribo-hex-5-enofuranose

Chemical Property of 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-3-C-methyl-α-D-ribo-hex-5-enofuranose

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Technology Process of 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-3-C-methyl-α-D-ribo-hex-5-enofuranose

There total 2 articles about 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-3-C-methyl-α-D-ribo-hex-5-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: 73.9%

3-O-benzyl-1,2-O-isopropylidene-3-C-methyl-5,6-ditosyloxy-α-D-allofuranose (98003-97-5) → 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-3-C-methyl-α-D-ribo-hex-5-enofuranose (98003-98-6)

Guidance literature:

With sodium iodide; In butanone; for 1.5h; Heating;

Reference yield:

3-O-Benzyl-3-C-methyl-1,2-O-isopropylidene-α-D-allofuranose (55533-86-3,120615-67-0) → 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-3-C-methyl-α-D-ribo-hex-5-enofuranose (98003-98-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 84.3 percent / DMAP, Et₃N / CH₂Cl₂ / 40 h / 0 - 20 °C

2: 73.9 percent / NaI / butan-2-one / 1.5 h / Heating

With dmap; triethylamine; sodium iodide; In dichloromethane; butanone;

Reference yield: 100.0%

3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-3-C-methyl-α-D-ribo-hex-5-enofuranose (98003-98-6) → 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-3-C-methyl-α-D-ribo-hexofuranose (64638-70-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 2h; Ambient temperature;

upstream raw materials:

3-O-benzyl-1,2-O-isopropylidene-3-C-methyl-5,6-ditosyloxy-α-D-allofuranose

3-O-Benzyl-3-C-methyl-1,2-O-isopropylidene-α-D-allofuranose

Downstream raw materials:

3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-3-C-methyl-α-D-ribo-hexofuranose

4,5-didesoxy-2-C-methyl-2-O-benzyl-3-O-formyl-D-erythro-al-pentose

(2S,3R,4S,5R)-1,3,4-trihydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylheptane

(2S,3R,4S,5R)-1-benzoyloxy-3,4-dihydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylheptane

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