6-O-benzyl-2-deoxy-3,4-O-isopropylidene-1-O-mesyl-2-mesylaminomethyl-β-D-psicofuranose

Base Information

Chemical Name:6-O-benzyl-2-deoxy-3,4-O-isopropylidene-1-O-mesyl-2-mesylaminomethyl-β-D-psicofuranose
CAS No.:876374-21-9
Molecular Formula:C₁₉H₂₉NO₉S₂
Molecular Weight:479.573
Hs Code.:

Synonyms:6-O-benzyl-2-deoxy-3,4-O-isopropylidene-1-O-mesyl-2-mesylaminomethyl-β-D-psicofuranose

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Chemical Property of 6-O-benzyl-2-deoxy-3,4-O-isopropylidene-1-O-mesyl-2-mesylaminomethyl-β-D-psicofuranose

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Technology Process of 6-O-benzyl-2-deoxy-3,4-O-isopropylidene-1-O-mesyl-2-mesylaminomethyl-β-D-psicofuranose

There total 5 articles about 6-O-benzyl-2-deoxy-3,4-O-isopropylidene-1-O-mesyl-2-mesylaminomethyl-β-D-psicofuranose 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: 66.0%

: 124-63-0
methanesulfonyl chloride

: 6-O-benzyl-2-deoxy-3,4-O-isopropylidene-2-aminomethyl-β-D-psicofuranose

: 876374-21-9
6-O-benzyl-2-deoxy-3,4-O-isopropylidene-1-O-mesyl-2-mesylaminomethyl-β-D-psicofuranose

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 16h;
DOI:10.1039/c8nj02777c

Reference yield:

: 145121-55-7
6-O-benzyl-3,4-O-isopropylidene-β-D-psicofuranosyl cyanide

: 876374-21-9
6-O-benzyl-2-deoxy-3,4-O-isopropylidene-1-O-mesyl-2-mesylaminomethyl-β-D-psicofuranose

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:

: 18422-54-3
1,2;4,5-di-O-isopropylidene-β-D-fructopyranose

: 876374-21-9
6-O-benzyl-2-deoxy-3,4-O-isopropylidene-1-O-mesyl-2-mesylaminomethyl-β-D-psicofuranose

Guidance literature:: Multi-step reaction with 5 steps

1.1: Amberlyst A₁₅ / acetone / 13 h

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

2.2: 4 h / 0 - 20 °C

3.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / -20 °C / Inert atmosphere

4.1: lithium aluminium tetrahydride / diethyl ether / 2.5 h / 0 - 20 °C / Inert atmosphere

5.1: triethylamine; dmap / dichloromethane / 16 h / 0 - 20 °C

With dmap; lithium aluminium tetrahydride; trimethylsilyl trifluoromethanesulfonate; sodium hydride; triethylamine; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; mineral oil;
DOI:10.1039/c8nj02777c