6,8-di-O-benzyl-5-deoxy-5-(2,4-dinitrophenylamino)-1,2-O-isopropylidene-7-O-methylsulfonyl-α-D-threo-D-allooctofuranose-(1,4)

Base Information

Chemical Name:6,8-di-O-benzyl-5-deoxy-5-(2,4-dinitrophenylamino)-1,2-O-isopropylidene-7-O-methylsulfonyl-α-D-threo-D-allooctofuranose-(1,4)
CAS No.:109748-39-2
Molecular Formula:C₃₂H₃₇N₃O₁₃S
Molecular Weight:703.724
Hs Code.:

Synonyms:6,8-di-O-benzyl-5-deoxy-5-(2,4-dinitrophenylamino)-1,2-O-isopropylidene-7-O-methylsulfonyl-α-D-threo-D-allooctofuranose-(1,4)

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Chemical Property of 6,8-di-O-benzyl-5-deoxy-5-(2,4-dinitrophenylamino)-1,2-O-isopropylidene-7-O-methylsulfonyl-α-D-threo-D-allooctofuranose-(1,4)

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Technology Process of 6,8-di-O-benzyl-5-deoxy-5-(2,4-dinitrophenylamino)-1,2-O-isopropylidene-7-O-methylsulfonyl-α-D-threo-D-allooctofuranose-(1,4)

There total 9 articles about 6,8-di-O-benzyl-5-deoxy-5-(2,4-dinitrophenylamino)-1,2-O-isopropylidene-7-O-methylsulfonyl-α-D-threo-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: 86.7%

: 109748-38-1
6,8-di-O-benzyl-5-deoxy-5-(2,4-dinitrophenylamino)-1,2-O-isopropylidene-7-O-methylsulfonyl-3-O-methylthiomethyl-α-D-threo-D-allooctofuranose-(1,4)

: 74-88-4
methyl iodide

: 109748-39-2
6,8-di-O-benzyl-5-deoxy-5-(2,4-dinitrophenylamino)-1,2-O-isopropylidene-7-O-methylsulfonyl-α-D-threo-D-allooctofuranose-(1,4)

Guidance literature:: With sodium hydrogencarbonate; In water; acetone; for 6h; Heating;
DOI:10.1246/bcsj.59.3523

Reference yield:

: 100-39-0
benzyl bromide

: 109748-39-2
6,8-di-O-benzyl-5-deoxy-5-(2,4-dinitrophenylamino)-1,2-O-isopropylidene-7-O-methylsulfonyl-α-D-threo-D-allooctofuranose-(1,4)

Guidance literature:: Multi-step reaction with 8 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

6: 1.) NaOH, 2.) triethylamine / 1.) 95 percent aq. 2-methoxy-ethanol, 1.5 h, reflux; 2.) THF, 12 h, r.t.

7: 86.9 percent / pyridine / Ambient temperature

8: 86.7 percent / NaHCO₃ / H₂O; acetone / 6 h / Heating

With sodium hydroxide; sodium hydride; sodium hydrogencarbonate; acetic acid; triethylamine; In tetrahydrofuran; pyridine; water; acetic acid; N,N-dimethyl-formamide; acetone;
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

: 109748-39-2
6,8-di-O-benzyl-5-deoxy-5-(2,4-dinitrophenylamino)-1,2-O-isopropylidene-7-O-methylsulfonyl-α-D-threo-D-allooctofuranose-(1,4)

Guidance literature:: Multi-step reaction with 8 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

6: 1.) NaOH, 2.) triethylamine / 1.) 95 percent aq. 2-methoxy-ethanol, 1.5 h, reflux; 2.) THF, 12 h, r.t.

7: 86.9 percent / pyridine / Ambient temperature

8: 86.7 percent / NaHCO₃ / H₂O; acetone / 6 h / Heating

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