2-(trimethylsilyl)ethyl (2-O-benzyl-4,6-O-benzylidene-3-O-chloroacetyl-β-D-galactopyranosyl)-(1→4)-2-O-benzoyl-3,6-di-O-benzyl-β-D-galactopyranoside

Base Information

Chemical Name:2-(trimethylsilyl)ethyl (2-O-benzyl-4,6-O-benzylidene-3-O-chloroacetyl-β-D-galactopyranosyl)-(1→4)-2-O-benzoyl-3,6-di-O-benzyl-β-D-galactopyranoside
CAS No.:1441128-04-6
Molecular Formula:C₅₄H₆₁ClO₁₃Si
Molecular Weight:981.609
Hs Code.:

2-(trimethylsilyl)ethyl (2-O-benzyl-4,6-O-benzylidene-3-O-chloroacetyl-β-D-galactopyranosyl)-(1→4)-2-O-benzoyl-3,6-di-O-benzyl-β-D-galactopyranoside

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Chemical Property of 2-(trimethylsilyl)ethyl (2-O-benzyl-4,6-O-benzylidene-3-O-chloroacetyl-β-D-galactopyranosyl)-(1→4)-2-O-benzoyl-3,6-di-O-benzyl-β-D-galactopyranoside

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Technology Process of 2-(trimethylsilyl)ethyl (2-O-benzyl-4,6-O-benzylidene-3-O-chloroacetyl-β-D-galactopyranosyl)-(1→4)-2-O-benzoyl-3,6-di-O-benzyl-β-D-galactopyranoside

There total 8 articles about 2-(trimethylsilyl)ethyl (2-O-benzyl-4,6-O-benzylidene-3-O-chloroacetyl-β-D-galactopyranosyl)-(1→4)-2-O-benzoyl-3,6-di-O-benzyl-β-D-galactopyranoside 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:

: ethyl 1-thio-2-O-benzyl-4,6-O-benzylidene-3-O-chloroacetyl-β-D-galactopyranoside

: 117253-09-5
2-(trimethylsilyl)ethyl 2-O-benzoyl-3,6-di-O-benzyl-β-D-galactopyranoside

: 1441127-99-6
2-(trimethylsilyl)ethyl (2-O-benzyl-4,6-O-benzylidene-3-O-chloroacetyl-α-D-galactopyranosyl)-(1→4)-2-O-benzoyl-3,6-di-O-benzyl-β-D-galactopyranoside

: 1441128-04-6
2-(trimethylsilyl)ethyl (2-O-benzyl-4,6-O-benzylidene-3-O-chloroacetyl-β-D-galactopyranosyl)-(1→4)-2-O-benzoyl-3,6-di-O-benzyl-β-D-galactopyranoside

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at -78 - -40 ℃; for 0.5h; Overall yield = 84 %; Overall yield = 197 mg; Inert atmosphere; Molecular sieve;
DOI:10.1002/chem.201203865

Reference yield:

: ethyl 2-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

: 1441127-99-6
2-(trimethylsilyl)ethyl (2-O-benzyl-4,6-O-benzylidene-3-O-chloroacetyl-α-D-galactopyranosyl)-(1→4)-2-O-benzoyl-3,6-di-O-benzyl-β-D-galactopyranoside

: 1441128-04-6
2-(trimethylsilyl)ethyl (2-O-benzyl-4,6-O-benzylidene-3-O-chloroacetyl-β-D-galactopyranosyl)-(1→4)-2-O-benzoyl-3,6-di-O-benzyl-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: pyridine / dichloromethane / 0.5 h / 20 °C

2: N-iodo-succinimide; trifluorormethanesulfonic acid / dichloromethane / 0.5 h / -78 - -40 °C / Inert atmosphere; Molecular sieve

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane;
DOI:10.1002/chem.201203865

Reference yield:

: 131564-36-8
ethyl (S)-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

: 1441127-99-6
2-(trimethylsilyl)ethyl (2-O-benzyl-4,6-O-benzylidene-3-O-chloroacetyl-α-D-galactopyranosyl)-(1→4)-2-O-benzoyl-3,6-di-O-benzyl-β-D-galactopyranoside

: 1441128-04-6
2-(trimethylsilyl)ethyl (2-O-benzyl-4,6-O-benzylidene-3-O-chloroacetyl-β-D-galactopyranosyl)-(1→4)-2-O-benzoyl-3,6-di-O-benzyl-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: di(n-butyl)tin oxide / toluene / 4 h / 20 - 140 °C

1.2: 12 h / 20 - 50 °C

2.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 0 °C

2.2: 2 h / 0 °C

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydrogencarbonate / dichloromethane; water / 6 h / 20 °C

4.1: pyridine / dichloromethane / 0.5 h / 20 °C

5.1: N-iodo-succinimide; trifluorormethanesulfonic acid / dichloromethane / 0.5 h / -78 - -40 °C / Inert atmosphere; Molecular sieve

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; sodium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1002/chem.201203865