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

Base Information

Chemical Name:5-acetamido-6-O-benzyl-5-deoxy-1,2:7,8-di-O-isopropylidene-3-O-methylthiomethyl-β-L-erythro-D-allooctofuranose-(1,4)
CAS No.:106191-26-8
Molecular Formula:C₂₅H₃₇NO₈S
Molecular Weight:511.637
Hs Code.:

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

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

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

There total 12 articles about 5-acetamido-6-O-benzyl-5-deoxy-1,2:7,8-di-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:

: 106180-08-9
5-deoxy-1,2-O-isopropylidene-3-O-<(methylthio)methyl>-5-nitro-α-D-ribofuranose

: 106191-26-8
5-acetamido-6-O-benzyl-5-deoxy-1,2:7,8-di-O-isopropylidene-3-O-methylthiomethyl-β-L-erythro-D-allooctofuranose-(1,4)

Guidance literature:: Multi-step reaction with 3 steps

1: KF, tetrabutylammonium iodide / toluene / 2.5 h / Ambient temperature

2: H₂ / Raney nickel T-4 / ethyl acetate; acetic acid / 20 h / 4045.3 Torr

3: 2.) NaH / 1.) methanol, room temp., 10 min.; 2.) DMF, 95 min.

With potassium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; Raney nickel T-4; In acetic acid; ethyl acetate; toluene;
DOI:10.1246/bcsj.59.1753

Reference yield:

: 106180-06-7
1,2-O-isopropylidene-3-O-methylthiomethyl-5-O-p-tolylsulfonyl-α-D-ribofuranose

: 106191-26-8
5-acetamido-6-O-benzyl-5-deoxy-1,2:7,8-di-O-isopropylidene-3-O-methylthiomethyl-β-L-erythro-D-allooctofuranose-(1,4)

Guidance literature:: Multi-step reaction with 5 steps

1: 93.9 percent / NaI / butan-2-one / 2 h / Heating

2: 54.2 percent / phloroglucinol monohydrate, sodium nitrite / dimethylsulfoxide / 96 h / Ambient temperature

3: KF, tetrabutylammonium iodide / toluene / 2.5 h / Ambient temperature

4: H₂ / Raney nickel T-4 / ethyl acetate; acetic acid / 20 h / 4045.3 Torr

5: 2.) NaH / 1.) methanol, room temp., 10 min.; 2.) DMF, 95 min.

With potassium fluoride; 3,5-dihydroxyphenol; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium iodide; sodium nitrite; Raney nickel T-4; In acetic acid; dimethyl sulfoxide; ethyl acetate; toluene; butanone;
DOI:10.1246/bcsj.59.1753

Reference yield:

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

: 106191-26-8
5-acetamido-6-O-benzyl-5-deoxy-1,2:7,8-di-O-isopropylidene-3-O-methylthiomethyl-β-L-erythro-D-allooctofuranose-(1,4)

Guidance literature:: Multi-step reaction with 2 steps

1: H₂ / Raney nickel T-4 / ethyl acetate; acetic acid / 20 h / 4045.3 Torr

2: 2.) NaH / 1.) methanol, room temp., 10 min.; 2.) DMF, 95 min.

With hydrogen; sodium hydride; Raney nickel T-4; In acetic acid; ethyl acetate;
DOI:10.1246/bcsj.59.1753