7,8,9-tri-O-acetyl-2,6-anhydro-4,5-O-carbonylidene-1,3-dideoxy-2-methyl-1-phenylseleno-D-erythro-L-talo-nonitol

Base Information

Chemical Name:7,8,9-tri-O-acetyl-2,6-anhydro-4,5-O-carbonylidene-1,3-dideoxy-2-methyl-1-phenylseleno-D-erythro-L-talo-nonitol
CAS No.:503544-21-6
Molecular Formula:C₂₃H₂₈O₁₀Se
Molecular Weight:543.429
Hs Code.:

Synonyms:7,8,9-tri-O-acetyl-2,6-anhydro-4,5-O-carbonylidene-1,3-dideoxy-2-methyl-1-phenylseleno-D-erythro-L-talo-nonitol

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Chemical Property of 7,8,9-tri-O-acetyl-2,6-anhydro-4,5-O-carbonylidene-1,3-dideoxy-2-methyl-1-phenylseleno-D-erythro-L-talo-nonitol

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Technology Process of 7,8,9-tri-O-acetyl-2,6-anhydro-4,5-O-carbonylidene-1,3-dideoxy-2-methyl-1-phenylseleno-D-erythro-L-talo-nonitol

There total 8 articles about 7,8,9-tri-O-acetyl-2,6-anhydro-4,5-O-carbonylidene-1,3-dideoxy-2-methyl-1-phenylseleno-D-erythro-L-talo-nonitol 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: 95.0%

: 108-24-7
acetic anhydride

: 503544-19-2
2,6-anhydro-4,5-O-carbonylidene-1,3-dideoxy-2-methyl-1-phenylseleno-D-erythro-L-talo-nonitol

: 503544-21-6
7,8,9-tri-O-acetyl-2,6-anhydro-4,5-O-carbonylidene-1,3-dideoxy-2-methyl-1-phenylseleno-D-erythro-L-talo-nonitol

Guidance literature:: With dmap; In pyridine; at 20 ℃; for 12h;
DOI:10.1016/S0008-6215(02)00176-3

Reference yield:

: 5707-04-0
Phenylselenyl chloride

: 503544-21-6
7,8,9-tri-O-acetyl-2,6-anhydro-4,5-O-carbonylidene-1,3-dideoxy-2-methyl-1-phenylseleno-D-erythro-L-talo-nonitol

Guidance literature:: Multi-step reaction with 2 steps

1: 61 percent / AgOTf; propionitrile / 1 h / -80 °C

2: 95 percent / DMAP / pyridine / 12 h / 20 °C

With dmap; silver trifluoromethanesulfonate; propiononitrile; In pyridine;
DOI:10.1016/S0008-6215(02)00176-3

Reference yield:

: 52492-60-1
1,2:3,4:5,6-tri-O-isopropylidene-δ-gluconolactone

: 503544-21-6
7,8,9-tri-O-acetyl-2,6-anhydro-4,5-O-carbonylidene-1,3-dideoxy-2-methyl-1-phenylseleno-D-erythro-L-talo-nonitol

Guidance literature:: Multi-step reaction with 7 steps

1: 87 percent / tetrahydrofuran; diethyl ether / 0.33 h / -95 °C

2: 92 percent / Zn(BH₄)2 / diethyl ether / 1 h / -10 °C

3: 88 percent / DMAP / pyridine; CH₂Cl₂ / 0.5 h / 0 - 20 °C

4: TFA / tetrahydrofuran; H₂O / 0.17 h / 20 °C

5: 1.79 g / TFA / tetrahydrofuran; H₂O / 1.17 h / 70 °C

6: 61 percent / AgOTf; propionitrile / 1 h / -80 °C

7: 95 percent / DMAP / pyridine / 12 h / 20 °C

With dmap; zinc(II) tetrahydroborate; silver trifluoromethanesulfonate; trifluoroacetic acid; propiononitrile; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; water;
DOI:10.1016/S0008-6215(02)00176-3