ethyl (benzyl 6,7-dideoxy-2,3-O-isopropylidene-4-O-trifluoromethylsulfonyl-α-D-talo-octopyranosid)uronate

Base Information

Chemical Name:ethyl (benzyl 6,7-dideoxy-2,3-O-isopropylidene-4-O-trifluoromethylsulfonyl-α-D-talo-octopyranosid)uronate
CAS No.:140428-30-4
Molecular Formula:C₂₁H₂₇F₃O₉S
Molecular Weight:512.501
Hs Code.:

Synonyms:ethyl (benzyl 6,7-dideoxy-2,3-O-isopropylidene-4-O-trifluoromethylsulfonyl-α-D-talo-octopyranosid)uronate

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Chemical Property of ethyl (benzyl 6,7-dideoxy-2,3-O-isopropylidene-4-O-trifluoromethylsulfonyl-α-D-talo-octopyranosid)uronate

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Technology Process of ethyl (benzyl 6,7-dideoxy-2,3-O-isopropylidene-4-O-trifluoromethylsulfonyl-α-D-talo-octopyranosid)uronate

There total 11 articles about ethyl (benzyl 6,7-dideoxy-2,3-O-isopropylidene-4-O-trifluoromethylsulfonyl-α-D-talo-octopyranosid)uronate 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: 88.0%

: 358-23-6
trifluoromethylsulfonic anhydride

: 140428-29-1
ethyl (benzyl 6,7-dideoxy-2,3-O-isopropylidene-α-D-talo-octopyranosid)uronate

: 140428-30-4
ethyl (benzyl 6,7-dideoxy-2,3-O-isopropylidene-4-O-trifluoromethylsulfonyl-α-D-talo-octopyranosid)uronate

Guidance literature:: With pyridine; In dichloromethane; at -20 ℃; for 15h;
DOI:10.1246/bcsj.65.567

Reference yield:

: 15548-45-5
(2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

: 140428-30-4
ethyl (benzyl 6,7-dideoxy-2,3-O-isopropylidene-4-O-trifluoromethylsulfonyl-α-D-talo-octopyranosid)uronate

Guidance literature:: Multi-step reaction with 10 steps

1: 75 percent / pyridine / CH₂Cl₂ / 2 h / Ambient temperature

2: 94.3 percent / 2-naphthalenesulfonic acid / acetone / 8 h / Ambient temperature

3: 94 percent / triethylamine / tetrahydrofuran / Ambient temperature

4: 1.) Na / 1.) toluene, reflux, 2.) toluene, reflux, overnight

5: 70 percent / DMSO, NaCl / H₂O / 15 h / 145 °C

6: 1 g / 1 M aq. KOH / methanol / Ambient temperature

7: 96 percent / diethyl ether

8: 95 percent / pyridinium chlorochromate (PCC) / CH₂Cl₂ / Ambient temperature

9: 97 percent / NaBH₄ / ethanol / 0.5 h / Ambient temperature

10: 88 percent / pyridine / CH₂Cl₂ / 15 h / -20 °C

With pyridine; potassium hydroxide; sodium tetrahydroborate; naphthalene-2-sulfonate; sodium; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; sodium chloride; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetone;
DOI:10.1246/bcsj.65.567

Reference yield:

: 117371-06-9
benzyl 6-O-p-toluenesulfonyl-α-D-mannopyranoside

: 140428-30-4
ethyl (benzyl 6,7-dideoxy-2,3-O-isopropylidene-4-O-trifluoromethylsulfonyl-α-D-talo-octopyranosid)uronate

Guidance literature:: Multi-step reaction with 9 steps

1: 94.3 percent / 2-naphthalenesulfonic acid / acetone / 8 h / Ambient temperature

2: 94 percent / triethylamine / tetrahydrofuran / Ambient temperature

3: 1.) Na / 1.) toluene, reflux, 2.) toluene, reflux, overnight

4: 70 percent / DMSO, NaCl / H₂O / 15 h / 145 °C

5: 1 g / 1 M aq. KOH / methanol / Ambient temperature

6: 96 percent / diethyl ether

7: 95 percent / pyridinium chlorochromate (PCC) / CH₂Cl₂ / Ambient temperature

8: 97 percent / NaBH₄ / ethanol / 0.5 h / Ambient temperature

9: 88 percent / pyridine / CH₂Cl₂ / 15 h / -20 °C

With pyridine; potassium hydroxide; sodium tetrahydroborate; naphthalene-2-sulfonate; sodium; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; sodium chloride; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetone;
DOI:10.1246/bcsj.65.567