5-acetamido-6,8-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-O-methylthiomethyl-α-D-threo-D-allooctofuranose

Base Information

Chemical Name:5-acetamido-6,8-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-O-methylthiomethyl-α-D-threo-D-allooctofuranose
CAS No.:109748-36-9
Molecular Formula:C₂₉H₃₉NO₈S
Molecular Weight:561.697
Hs Code.:

Synonyms:5-acetamido-6,8-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-O-methylthiomethyl-α-D-threo-D-allooctofuranose

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Chemical Property of 5-acetamido-6,8-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-O-methylthiomethyl-α-D-threo-D-allooctofuranose

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Technology Process of 5-acetamido-6,8-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-O-methylthiomethyl-α-D-threo-D-allooctofuranose

There total 6 articles about 5-acetamido-6,8-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-O-methylthiomethyl-α-D-threo-D-allooctofuranose 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: 92.3%

: 109748-35-8
5-acetamido-6,8-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-7-O-methylsulfonyl-3-O-methylthiomethyl-β-L-erythro-D-allooctofuranose-(1,4)

: 109748-36-9
5-acetamido-6,8-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-O-methylthiomethyl-α-D-threo-D-allooctofuranose

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; for 0.666667h; Ambient temperature;
DOI:10.1246/bcsj.59.3523

Reference yield:

: 100-39-0
benzyl bromide

: 109748-36-9
5-acetamido-6,8-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-O-methylthiomethyl-α-D-threo-D-allooctofuranose

Guidance literature:: Multi-step reaction with 5 steps

1: 49 percent / NaH / dimethylformamide

2: aq. acetic acid / aq. acetic acid / Ambient temperature

3: 48.6 percent / NaH / tetrahydrofuran / 12 h / 5 °C

4: 78 percent / pyridine / 2 h / Ambient temperature

5: 92.3 percent / NaH / dimethylformamide / 0.67 h / Ambient temperature

With sodium hydride; acetic acid; In tetrahydrofuran; pyridine; acetic acid; N,N-dimethyl-formamide;
DOI:10.1246/bcsj.59.3523

Reference yield:

: N-[(R)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-1-((3aR,5R,6R,6aR)-2,2-dimethyl-6-methylsulfanylmethoxy-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-ethyl]-acetamide

: 109748-36-9
5-acetamido-6,8-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-O-methylthiomethyl-α-D-threo-D-allooctofuranose

Guidance literature:: Multi-step reaction with 5 steps

1: 49 percent / NaH / dimethylformamide

2: aq. acetic acid / aq. acetic acid / Ambient temperature

3: 48.6 percent / NaH / tetrahydrofuran / 12 h / 5 °C

4: 78 percent / pyridine / 2 h / Ambient temperature

5: 92.3 percent / NaH / dimethylformamide / 0.67 h / Ambient temperature

With sodium hydride; acetic acid; In tetrahydrofuran; pyridine; acetic acid; N,N-dimethyl-formamide;
DOI:10.1246/bcsj.59.3523