3,4-di-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl trichloroacetimidate

Base Information

Chemical Name:3,4-di-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl trichloroacetimidate
CAS No.:139526-03-7
Molecular Formula:C₂₇H₂₅Cl₃N₂O₉
Molecular Weight:627.862
Hs Code.:

Synonyms:3,4-di-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl trichloroacetimidate

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Chemical Property of 3,4-di-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl trichloroacetimidate

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Technology Process of 3,4-di-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl trichloroacetimidate

There total 7 articles about 3,4-di-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl trichloroacetimidate 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: 90.0%

: 3,4-di-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-D-galactopyranoside

: 545-06-2
trichloroacetonitrile

: 139526-03-7
3,4-di-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; for 2h; 0 deg C to RT;
DOI:10.1021/jo00032a601

Reference yield:

: 138906-43-1
4-methoxyphenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

: 139526-03-7
3,4-di-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 7 steps

1: 89 percent / NEt₃ / 1,2-dichloro-ethane / 5 h / Ambient temperature

2: 78 percent / BH₃*Me₃N, AlCl₃, molecular sieve 4A / tetrahydrofuran / Ambient temperature

3: 81 percent / Et₂NSF₃ / tetrahydrofuran / 50 °C

4: 95 percent / 1M NaOMe / methanol; CH₂Cl₂ / 0 °C

5: pyridine, 4-dimethylaminopyridine / Ambient temperature

6: ceric ammonium nitrate / toluene; acetonitrile; H₂O / 1 h / Ambient temperature

7: 90 percent / DBU / toluene / 2 h / 0 deg C to RT

With pyridine; dmap; aluminium trichloride; ammonium cerium(IV) nitrate; diethylamino-sulfur trifluoride; trimethylamine-borane; 4 A molecular sieve; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; toluene; acetonitrile;
DOI:10.1021/jo00032a601

Reference yield:

: 139526-00-4
p-methoxyphenyl 6-O-benzyl-2-deoxy-2-N-phthalimido-β-D-galactopyranoside

: 139526-03-7
3,4-di-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 3 steps

1: pyridine, 4-dimethylaminopyridine / Ambient temperature

2: ceric ammonium nitrate / toluene; acetonitrile; H₂O / 1 h / Ambient temperature

3: 90 percent / DBU / toluene / 2 h / 0 deg C to RT

With pyridine; dmap; ammonium cerium(IV) nitrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In water; toluene; acetonitrile;
DOI:10.1021/jo00032a601