(4'S,5'R,6'R)-(+)-4-5'-benzyloxy-6'-benzyloxymethyl-1',3'-dioxan-4'-yl-2,6-piperidinedione

Base Information

Chemical Name:(4'S,5'R,6'R)-(+)-4-5'-benzyloxy-6'-benzyloxymethyl-1',3'-dioxan-4'-yl-2,6-piperidinedione
CAS No.:120786-90-5
Molecular Formula:C₂₄H₂₇NO₆
Molecular Weight:425.481
Hs Code.:

Synonyms:

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Chemical Property of (4'S,5'R,6'R)-(+)-4-5'-benzyloxy-6'-benzyloxymethyl-1',3'-dioxan-4'-yl-2,6-piperidinedione

Chemical Property:

Purity/Quality:

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Technology Process of (4'S,5'R,6'R)-(+)-4-5'-benzyloxy-6'-benzyloxymethyl-1',3'-dioxan-4'-yl-2,6-piperidinedione

There total 34 articles about (4'S,5'R,6'R)-(+)-4-5'-benzyloxy-6'-benzyloxymethyl-1',3'-dioxan-4'-yl-2,6-piperidinedione 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:

: 41546-31-0
L-xylose

: 120786-90-5
4-((4R,5S,6S)-5-Benzyloxy-6-benzyloxymethyl-[1,3]dioxan-4-yl)-piperidine-2,6-dione

Guidance literature:: Multi-step reaction with 11 steps

2: 1.) NaH / 1.) THF, reflux, 15 min, 2.) Bu₄NBr, reflux, 5 min

3: 12N-HCl / acetic acid / 0.08 h / Ambient temperature

4: toluene / 0.5 h / Heating

5: trimethylsilyl trifluoromethanesulfonate / 0.25 h / 0 °C

6: Bu₄NBr / tetrahydrofuran / 12 h / 40 °C

7: NaCl, H₂O / dimethylsulfoxide / 1 h / 160 °C

8: 1N-KOH / methanol / 48 h / Ambient temperature

9: MeOCOCl, Et₃N / tetrahydrofuran / 3 h / -20 °C

10: NH₃ (gas) / 0.5 h / 0 °C

11: NaOAc, Ac₂O / 0.33 h / 100 °C

With hydrogenchloride; potassium hydroxide; trimethylsilyl trifluoromethanesulfonate; ammonia; water; sodium acetate; acetic anhydride; sodium hydride; triethylamine; methyl chloroformate; sodium chloride; tetrabutylammomium bromide; In tetrahydrofuran; methanol; acetic acid; dimethyl sulfoxide; toluene;
DOI:10.1016/S0040-4039(00)98773-2

Reference yield:

: 16054-77-6,120693-82-5,120693-83-6
3,5-di-O-benzyl-L-xylofuranose

: 120786-90-5
4-((4R,5S,6S)-5-Benzyloxy-6-benzyloxymethyl-[1,3]dioxan-4-yl)-piperidine-2,6-dione

Guidance literature:: Multi-step reaction with 8 steps

1: toluene / 0.5 h / Heating

2: trimethylsilyl trifluoromethanesulfonate / 0.25 h / 0 °C

3: Bu₄NBr / tetrahydrofuran / 12 h / 40 °C

4: NaCl, H₂O / dimethylsulfoxide / 1 h / 160 °C

5: 1N-KOH / methanol / 48 h / Ambient temperature

6: MeOCOCl, Et₃N / tetrahydrofuran / 3 h / -20 °C

7: NH₃ (gas) / 0.5 h / 0 °C

8: NaOAc, Ac₂O / 0.33 h / 100 °C

With potassium hydroxide; trimethylsilyl trifluoromethanesulfonate; ammonia; water; sodium acetate; acetic anhydride; triethylamine; methyl chloroformate; sodium chloride; tetrabutylammomium bromide; In tetrahydrofuran; methanol; dimethyl sulfoxide; toluene;
DOI:10.1016/S0040-4039(00)98773-2

Reference yield:

: 100-44-7
benzyl chloride

: 120786-90-5
4-((4R,5S,6S)-5-Benzyloxy-6-benzyloxymethyl-[1,3]dioxan-4-yl)-piperidine-2,6-dione

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) NaH / 1.) THF, reflux, 15 min, 2.) Bu₄NBr, reflux, 5 min

2: 12N-HCl / acetic acid / 0.08 h / Ambient temperature

3: toluene / 0.5 h / Heating

4: trimethylsilyl trifluoromethanesulfonate / 0.25 h / 0 °C

5: Bu₄NBr / tetrahydrofuran / 12 h / 40 °C

6: NaCl, H₂O / dimethylsulfoxide / 1 h / 160 °C

7: 1N-KOH / methanol / 48 h / Ambient temperature

8: MeOCOCl, Et₃N / tetrahydrofuran / 3 h / -20 °C

9: NH₃ (gas) / 0.5 h / 0 °C

10: NaOAc, Ac₂O / 0.33 h / 100 °C

With hydrogenchloride; potassium hydroxide; trimethylsilyl trifluoromethanesulfonate; ammonia; water; sodium acetate; acetic anhydride; sodium hydride; triethylamine; methyl chloroformate; sodium chloride; tetrabutylammomium bromide; In tetrahydrofuran; methanol; acetic acid; dimethyl sulfoxide; toluene;
DOI:10.1016/S0040-4039(00)98773-2