3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-C--α-D-xylo-hexofuranos-5-ulose

Base Information

• Chemical Name: 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-C--α-D-xylo-hexofuranos-5-ulose
• CAS No.: 88151-65-9
• Molecular Formula: C₄₄H₄₈O₁₀
• Molecular Weight: 736.859

Synonyms:3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-C--α-D-xylo-hexofuranos-5-ulose

Chemical Property of 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-C--α-D-xylo-hexofuranos-5-ulose

Chemical Property:

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Technology Process of 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-C--α-D-xylo-hexofuranos-5-ulose

There total 3 articles about 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-C--α-D-xylo-hexofuranos-5-ulose 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:

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) → 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-C--α-D-xylo-hexofuranos-5-ulose (88151-65-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / Jones reagent / acetone

3: benzene / 5 h / Heating

With jones reagent; In acetone; benzene;

DOI:10.1016/0008-6215(92)84094-9

Reference yield:

(3aR,5S,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuran[2,3-d][1,3]dioxolane-5-carboxylic acid (39682-04-7) → 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-C--α-D-xylo-hexofuranos-5-ulose (88151-65-9)

Guidance literature:

Multi-step reaction with 2 steps

2: benzene / 5 h / Heating

In benzene;

DOI:10.1016/0008-6215(92)84094-9

Reference yield:

methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside (83051-88-1) + 1-((3aR,5S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(triphenyl-λ5-phosphanylidene)-ethanone (140138-24-5) → 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-C--α-D-xylo-hexofuranos-5-ulose (88151-65-9)

Guidance literature:

In benzene; for 5h; Yield given; Heating;

DOI:10.1016/0008-6215(92)84094-9

upstream raw materials:

methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside

1-((3aR,5S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(triphenyl-λ⁵-phosphanylidene)-ethanone

(3aR,5S,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuran[2,3-d][1,3]dioxolane-5-carboxylic acid

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

Downstream raw materials:

3-O-benzyl-1,2-O-isopropylidene-6-C--L-glycero-α-D-gluco-hexofuranose

3-O-benzyl-1,2-O-isopropylidene-6-C--D-glycero-α-D-gluco-hexofuranose

3-O-benzyl-1,2-O-isopropylidene-6-C--α-D-gluco-hexofuranos-5-ulose

3-O-benzyl-1,2-O-isopropylidene-6-C--β-L-ido-hexofuranos-5-ulose

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