2,4,6-tri-O-benzoyl-3-O-<2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate>-α-D-galactopyranosyl trichloroacetimidate

Base Information

Chemical Name:2,4,6-tri-O-benzoyl-3-O-<2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate>-α-D-galactopyranosyl trichloroacetimidate
CAS No.:152088-98-7
Molecular Formula:C₆₁H₅₆Cl₃NO₁₈Si
Molecular Weight:1225.56
Hs Code.:

2,4,6-tri-O-benzoyl-3-O-<2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate>-α-D-galactopyranosyl trichloroacetimidate

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Chemical Property of 2,4,6-tri-O-benzoyl-3-O-<2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate>-α-D-galactopyranosyl trichloroacetimidate

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Technology Process of 2,4,6-tri-O-benzoyl-3-O-<2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate>-α-D-galactopyranosyl trichloroacetimidate

There total 9 articles about 2,4,6-tri-O-benzoyl-3-O-<2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate>-α-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:

: 87924-24-1
benzyl 2,3,4-tri-O-benzoyl-β-D-glucopyranoside

: 152088-98-7
2,4,6-tri-O-benzoyl-3-O-<2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate>-α-D-galactopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 10 steps

1: CrO₃, conc.H₂SO₄, H₂O / acetone / 2 h / 0 °C

2: oxalyl chloride, pyridine / CH₂Cl₂ / 0.5 h / 0 °C

3: pyridine / 1 h / 0 °C

4: H₂ / 10percent Pd-C / ethyl acetate / 16 h

5: 1,8-diazabicyclo<5,4,0>undec-7-ene / CH₂Cl₂ / 0.25 h / Ambient temperature

6: 1) activated 4A molecular sieves, 2) trimethylsilyl triflate / 1) 1,2-dichloroethane, r.t., 2) toluene, 0 degC, 15 min

7: acetic acid, water / 1,2-dimethoxy-ethane / 0.5 h / 100 °C

8: 4-dimethylaminopyridine, pyridine / 1 h / Ambient temperature

9: H₂ / 10percent Pd-C / ethyl acetate / 16 h

10: 1,8-diazabicyclo<5,4,0>undec-7-ene / CH₂Cl₂ / 0.25 h / Ambient temperature

With pyridine; chromium(VI) oxide; dmap; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sulfuric acid; water; hydrogen; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In 1,2-dimethoxyethane; dichloromethane; ethyl acetate; acetone;
DOI:10.1016/0008-6215(83)85009-5

Reference yield:

: (2S,3S,4S,5R,6R)-3,4,5-Tris-benzoyloxy-6-hydroxy-tetrahydro-pyran-2-carboxylic acid 2-trimethylsilanyl-ethyl ester

: 152088-98-7
2,4,6-tri-O-benzoyl-3-O-<2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate>-α-D-galactopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 6 steps

1: 1,8-diazabicyclo<5,4,0>undec-7-ene / CH₂Cl₂ / 0.25 h / Ambient temperature

2: 1) activated 4A molecular sieves, 2) trimethylsilyl triflate / 1) 1,2-dichloroethane, r.t., 2) toluene, 0 degC, 15 min

3: acetic acid, water / 1,2-dimethoxy-ethane / 0.5 h / 100 °C

4: 4-dimethylaminopyridine, pyridine / 1 h / Ambient temperature

5: H₂ / 10percent Pd-C / ethyl acetate / 16 h

6: 1,8-diazabicyclo<5,4,0>undec-7-ene / CH₂Cl₂ / 0.25 h / Ambient temperature

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; water; hydrogen; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In 1,2-dimethoxyethane; dichloromethane; ethyl acetate;
DOI:10.1016/0008-6215(83)85009-5

Reference yield:

: (2S,3S,4S,5R,6R)-3,4,5-Tris-benzoyloxy-6-benzyloxy-tetrahydro-pyran-2-carboxylic acid

: 152088-98-7
2,4,6-tri-O-benzoyl-3-O-<2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate>-α-D-galactopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 9 steps

1: oxalyl chloride, pyridine / CH₂Cl₂ / 0.5 h / 0 °C

2: pyridine / 1 h / 0 °C

3: H₂ / 10percent Pd-C / ethyl acetate / 16 h

4: 1,8-diazabicyclo<5,4,0>undec-7-ene / CH₂Cl₂ / 0.25 h / Ambient temperature

5: 1) activated 4A molecular sieves, 2) trimethylsilyl triflate / 1) 1,2-dichloroethane, r.t., 2) toluene, 0 degC, 15 min

6: acetic acid, water / 1,2-dimethoxy-ethane / 0.5 h / 100 °C

7: 4-dimethylaminopyridine, pyridine / 1 h / Ambient temperature

8: H₂ / 10percent Pd-C / ethyl acetate / 16 h

9: 1,8-diazabicyclo<5,4,0>undec-7-ene / CH₂Cl₂ / 0.25 h / Ambient temperature

With pyridine; dmap; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; water; hydrogen; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In 1,2-dimethoxyethane; dichloromethane; ethyl acetate;
DOI:10.1016/0008-6215(83)85009-5