5-acetamido-8-O-allyl-6-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-O-methylthiomethyl-β-L-erythro-D-allooctofuranose-(1,4)

Base Information

Chemical Name:5-acetamido-8-O-allyl-6-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-O-methylthiomethyl-β-L-erythro-D-allooctofuranose-(1,4)
CAS No.:112289-33-5
Molecular Formula:C₂₅H₃₇NO₈S
Molecular Weight:511.637
Hs Code.:

Synonyms:5-acetamido-8-O-allyl-6-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-O-methylthiomethyl-β-L-erythro-D-allooctofuranose-(1,4)

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Chemical Property of 5-acetamido-8-O-allyl-6-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-O-methylthiomethyl-β-L-erythro-D-allooctofuranose-(1,4)

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Technology Process of 5-acetamido-8-O-allyl-6-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-O-methylthiomethyl-β-L-erythro-D-allooctofuranose-(1,4)

There total 1 articles about 5-acetamido-8-O-allyl-6-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-O-methylthiomethyl-β-L-erythro-D-allooctofuranose-(1,4) 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: 64.5%

: 106-95-6
allyl bromide

: 106180-13-6
5-acetamido-6-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-O-methylthiomethyl-β-L-erythro-D-allooctofuranose-(1,4)

: 112289-33-5
5-acetamido-8-O-allyl-6-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-O-methylthiomethyl-β-L-erythro-D-allooctofuranose-(1,4)

Guidance literature:: With sodium hydride; In tetrahydrofuran; for 40h;
DOI:10.1246/bcsj.60.1057

Reference yield:

: 112289-33-5
5-acetamido-8-O-allyl-6-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-O-methylthiomethyl-β-L-erythro-D-allooctofuranose-(1,4)

: 1,2,3,7-tetra-O-acetyl-8-O-allyl-6-O-benzyl-5-deoxy-5-(2,4-dinitrophenylamino)-β-D-threo-D-allooctofuranose-(1,4)

Guidance literature:: Multi-step reaction with 6 steps

1: pyridine / 14 h

2: NaH / dimethylformamide / 1.5 h / Ambient temperature

3: NaOH, H₂O / various solvent(s) / 1.5 h / Heating

4: Et₃N / tetrahydrofuran / 1.5 h / Ambient temperature

5: 90percent trifluoroacetic acid / H₂O / 1.25 h / Ambient temperature

6: pyridine / 1 h / Ambient temperature

With pyridine; sodium hydroxide; water; sodium hydride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; water; N,N-dimethyl-formamide;
DOI:10.1246/bcsj.60.1057

Reference yield:

: 112289-33-5
5-acetamido-8-O-allyl-6-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-O-methylthiomethyl-β-L-erythro-D-allooctofuranose-(1,4)

: 112302-54-2
5-acetamido-8-O-allyl-6-O-benzyl-5-deoxy-1,2-O-isopropylidene-3-O-methylthiomethyl-α-D-threo-D-allooctofuranose-(1,4)

Guidance literature:: Multi-step reaction with 2 steps

1: pyridine / 14 h

2: NaH / dimethylformamide / 1.5 h / Ambient temperature

With pyridine; sodium hydride; In N,N-dimethyl-formamide;
DOI:10.1246/bcsj.60.1057