3-O-benzyl-2-deoxy-4,5-O-isopropylidene-1-O-mesyl-2-mesylaminomethyl-β-D-fructopyranose

Base Information

• Chemical Name: 3-O-benzyl-2-deoxy-4,5-O-isopropylidene-1-O-mesyl-2-mesylaminomethyl-β-D-fructopyranose
• CAS No.: 876374-19-5
• Molecular Formula: C₁₉H₂₉NO₉S₂
• Molecular Weight: 479.573

Synonyms:3-O-benzyl-2-deoxy-4,5-O-isopropylidene-1-O-mesyl-2-mesylaminomethyl-β-D-fructopyranose

Chemical Property of 3-O-benzyl-2-deoxy-4,5-O-isopropylidene-1-O-mesyl-2-mesylaminomethyl-β-D-fructopyranose

Chemical Property:

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Technology Process of 3-O-benzyl-2-deoxy-4,5-O-isopropylidene-1-O-mesyl-2-mesylaminomethyl-β-D-fructopyranose

There total 2 articles about 3-O-benzyl-2-deoxy-4,5-O-isopropylidene-1-O-mesyl-2-mesylaminomethyl-β-D-fructopyranose 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:

(3aR,6R,7S,7aR)-7-Benzyloxy-6-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carbonitrile (364635-38-1) → 3-O-benzyl-2-deoxy-4,5-O-isopropylidene-1-O-mesyl-2-mesylaminomethyl-β-D-fructopyranose (876374-19-5)

Guidance literature:

Multi-step reaction with 2 steps

1: LiAlH₄ / diethyl ether / 0 - 20 °C

2: pyridine / 24 h / 20 °C

With pyridine; lithium aluminium tetrahydride; In diethyl ether;

DOI:10.1016/j.tet.2005.10.038

Reference yield:

methanesulfonyl chloride (124-63-0) + ((3aR,6R,7S,7aR)-6-Aminomethyl-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-methanol → 3-O-benzyl-2-deoxy-4,5-O-isopropylidene-1-O-mesyl-2-mesylaminomethyl-β-D-fructopyranose (876374-19-5)

Guidance literature:

With pyridine; at 20 ℃; for 24h;

DOI:10.1016/j.tet.2005.10.038

Reference yield: 64.0%

3-O-benzyl-2-deoxy-4,5-O-isopropylidene-1-O-mesyl-2-mesylaminomethyl-β-D-fructopyranose (876374-19-5) → (7R,8R,9S)-2-aza-9-benzyloxy-7,8-(dimethylmethylenedioxy)-2-N-mesyl-5-oxaspiro[3.5]nonane (876374-20-8)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 2.5h;

DOI:10.1016/j.tet.2005.10.038

upstream raw materials:

methanesulfonyl chloride

(3aR,6R,7S,7aR)-7-Benzyloxy-6-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carbonitrile

Downstream raw materials:

(7R,8R,9S)-2-aza-9-benzyloxy-7,8-(dimethylmethylenedioxy)-2-N-mesyl-5-oxaspiro[3.5]nonane

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