methyl 4,7,8-tri-O-acetyl-9-O-benzoyl-1-O-benzyloxycarbonyl-3,5-dideoxy-5-trichloroacetamido-β-D-glycero-D-galacto-2-nonulopyranoside

Base Information

Chemical Name:methyl 4,7,8-tri-O-acetyl-9-O-benzoyl-1-O-benzyloxycarbonyl-3,5-dideoxy-5-trichloroacetamido-β-D-glycero-D-galacto-2-nonulopyranoside
CAS No.:160766-07-4
Molecular Formula:C₃₃H₃₆Cl₃NO₁₄
Molecular Weight:777.006
Hs Code.:

Synonyms:methyl 4,7,8-tri-O-acetyl-9-O-benzoyl-1-O-benzyloxycarbonyl-3,5-dideoxy-5-trichloroacetamido-β-D-glycero-D-galacto-2-nonulopyranoside

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Chemical Property of methyl 4,7,8-tri-O-acetyl-9-O-benzoyl-1-O-benzyloxycarbonyl-3,5-dideoxy-5-trichloroacetamido-β-D-glycero-D-galacto-2-nonulopyranoside

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Technology Process of methyl 4,7,8-tri-O-acetyl-9-O-benzoyl-1-O-benzyloxycarbonyl-3,5-dideoxy-5-trichloroacetamido-β-D-glycero-D-galacto-2-nonulopyranoside

There total 12 articles about methyl 4,7,8-tri-O-acetyl-9-O-benzoyl-1-O-benzyloxycarbonyl-3,5-dideoxy-5-trichloroacetamido-β-D-glycero-D-galacto-2-nonulopyranoside 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: 92.0%

: 108-24-7
acetic anhydride

: 160766-06-3
methyl 9-O-benzoyl-1-O-benzyloxycarbonyl-3,5-dideoxy-5-trichloroacetamido-β-D-glycero-D-galacto-2-nonulopyranoside

: 160766-07-4
methyl 4,7,8-tri-O-acetyl-9-O-benzoyl-1-O-benzyloxycarbonyl-3,5-dideoxy-5-trichloroacetamido-β-D-glycero-D-galacto-2-nonulopyranoside

Guidance literature:: With pyridine; for 12h; Ambient temperature;

Reference yield:

: 160765-91-3
(4Z)-3,4,5-trideoxy-1,2:7,8-di-O-isopropylidene-D-manno-non-4-enitol

: 160766-07-4
methyl 4,7,8-tri-O-acetyl-9-O-benzoyl-1-O-benzyloxycarbonyl-3,5-dideoxy-5-trichloroacetamido-β-D-glycero-D-galacto-2-nonulopyranoside

Guidance literature:: Multi-step reaction with 10 steps

1: 88 percent / Et₃N / acetonitrile / 1 h / -35 °C

2: 89 percent / 3-chloroperoxybenzoic acid / CH₂Cl₂ / 12.3 h / -10 °C

3: 77 percent / NaH, MgSO₄ / CH₂Cl₂ / 10 h

4: 92 percent / 0.3M BF₃*OEt₂ / CH₂Cl₂ / 1 h / 0 °C

5: 83 percent / TsOH*H₂O / pyridine; H₂O / 12 h / 80 °C

6: 82 percent / TsOH*H₂O / methanol / 4 h

7: 63 percent / (Bu₃Sn)2O, 2M Br₂ / CH₂Cl₂ / 1 h / 0 °C

8: 60 percent / Et₃N / CH₂Cl₂ / 0.17 h / -5 °C

9: 25 percent / satd. HCl / 1.5 h / -10 °C

10: 92 percent / pyridine / 12 h / Ambient temperature

With pyridine; hydrogenchloride; boron trifluoride diethyl etherate; bromine; sodium hydride; magnesium sulfate; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; bis(tri-n-butyltin)oxide; In pyridine; methanol; dichloromethane; water; acetonitrile;

Reference yield:

: 160765-90-2
(5Z)-5,6,7-trideoxy-2,3:8,9-di-O-isopropylidene-α-D-manno-non-5-enofuranose

: 160766-07-4
methyl 4,7,8-tri-O-acetyl-9-O-benzoyl-1-O-benzyloxycarbonyl-3,5-dideoxy-5-trichloroacetamido-β-D-glycero-D-galacto-2-nonulopyranoside

Guidance literature:: Multi-step reaction with 11 steps

1: 93 percent / NaBH₄ / ethanol / 1 h / 55 °C

2: 88 percent / Et₃N / acetonitrile / 1 h / -35 °C

3: 89 percent / 3-chloroperoxybenzoic acid / CH₂Cl₂ / 12.3 h / -10 °C

4: 77 percent / NaH, MgSO₄ / CH₂Cl₂ / 10 h

5: 92 percent / 0.3M BF₃*OEt₂ / CH₂Cl₂ / 1 h / 0 °C

6: 83 percent / TsOH*H₂O / pyridine; H₂O / 12 h / 80 °C

7: 82 percent / TsOH*H₂O / methanol / 4 h

8: 63 percent / (Bu₃Sn)2O, 2M Br₂ / CH₂Cl₂ / 1 h / 0 °C

9: 60 percent / Et₃N / CH₂Cl₂ / 0.17 h / -5 °C

10: 25 percent / satd. HCl / 1.5 h / -10 °C

11: 92 percent / pyridine / 12 h / Ambient temperature

With pyridine; hydrogenchloride; sodium tetrahydroborate; boron trifluoride diethyl etherate; bromine; sodium hydride; magnesium sulfate; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; bis(tri-n-butyltin)oxide; In pyridine; methanol; ethanol; dichloromethane; water; acetonitrile;