3-O-benzyl-1,2:5,6-di-O-isopropylidene-3-C-(3-mesyloxy)propyl-α-D-allofuranose

Base Information

Chemical Name:3-O-benzyl-1,2:5,6-di-O-isopropylidene-3-C-(3-mesyloxy)propyl-α-D-allofuranose
CAS No.:774598-90-2
Molecular Formula:C₂₃H₃₄O₉S
Molecular Weight:486.584
Hs Code.:

Synonyms:3-O-benzyl-1,2:5,6-di-O-isopropylidene-3-C-(3-mesyloxy)propyl-α-D-allofuranose

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Chemical Property of 3-O-benzyl-1,2:5,6-di-O-isopropylidene-3-C-(3-mesyloxy)propyl-α-D-allofuranose

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Technology Process of 3-O-benzyl-1,2:5,6-di-O-isopropylidene-3-C-(3-mesyloxy)propyl-α-D-allofuranose

There total 4 articles about 3-O-benzyl-1,2:5,6-di-O-isopropylidene-3-C-(3-mesyloxy)propyl-α-D-allofuranose 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: 79.0%

: 774598-89-9
3-O-benzyl-1,2:5,6-di-O-isopropylidene-3-C-(3-hydroxy)propyl-α-D-allofuranose

: 124-63-0
methanesulfonyl chloride

: 774598-90-2
3-O-benzyl-1,2:5,6-di-O-isopropylidene-3-C-(3-mesyloxy)propyl-α-D-allofuranose

Guidance literature:: With pyridine; at 20 ℃; for 3h;
DOI:10.1021/jo049159a

Reference yield:

: 100-39-0
benzyl bromide

: 774598-90-2
3-O-benzyl-1,2:5,6-di-O-isopropylidene-3-C-(3-mesyloxy)propyl-α-D-allofuranose

Guidance literature:: Multi-step reaction with 3 steps

1.1: 95 percent / NaH / dimethylformamide / 3 h / 20 °C

2.1: BH₃*Me₂S / tetrahydrofuran; diethyl ether / 4 h / 20 °C

2.2: 46 percent / aq. NaOH; H₂O₂ / tetrahydrofuran; diethyl ether / 67 h / 20 °C

3.1: 79 percent / pyridine / 3 h / 20 °C

With pyridine; dimethylsulfide borane complex; sodium hydride; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/jo049159a

Reference yield:

: 175877-45-9
3-C-allyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

: 774598-90-2
3-O-benzyl-1,2:5,6-di-O-isopropylidene-3-C-(3-mesyloxy)propyl-α-D-allofuranose

Guidance literature:: Multi-step reaction with 3 steps

1.1: 95 percent / NaH / dimethylformamide / 3 h / 20 °C

2.1: BH₃*Me₂S / tetrahydrofuran; diethyl ether / 4 h / 20 °C

2.2: 46 percent / aq. NaOH; H₂O₂ / tetrahydrofuran; diethyl ether / 67 h / 20 °C

3.1: 79 percent / pyridine / 3 h / 20 °C

With pyridine; dimethylsulfide borane complex; sodium hydride; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/jo049159a