2-(trimethylsilyl)ethyl 4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

Base Information

Chemical Name:2-(trimethylsilyl)ethyl 4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside
CAS No.:904690-73-9
Molecular Formula:C₃₇H₄₈ClN₃O₁₃Si
Molecular Weight:806.339
Hs Code.:

Synonyms:2-(trimethylsilyl)ethyl 4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

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Chemical Property of 2-(trimethylsilyl)ethyl 4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

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Technology Process of 2-(trimethylsilyl)ethyl 4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

There total 11 articles about 2-(trimethylsilyl)ethyl 4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside 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:

: Benzoic acid (2R,3R,4R,5S,6S)-4-[(2R,3R,4R,5S,6R)-3-azido-4-(2-chloro-acetoxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy]-5-benzyloxy-6-methyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

: 108-24-7
acetic anhydride

: 904690-73-9
2-(trimethylsilyl)ethyl 4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: With dmap; In pyridine; at 22 ℃; for 1h;
DOI:10.1016/j.carres.2006.04.006

Reference yield:

: (2R,3R,4S,5R,6S)-5-Benzyloxy-6-methyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3,4-diol

: 904690-73-9
2-(trimethylsilyl)ethyl 4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 141 g / camphorsulfonic acid / CH₂Cl₂ / 2 h / 22 °C

2: 82 percent / N-iodosuccinimide; TMSOTf / CH₂Cl₂ / 5 h / 0 - 22 °C

3: AcOH; aq. HCl / 0.33 h / 22 °C

4: 13.5 g / 4-dimethylaminopyridine / pyridine / 1 h / 22 °C

With hydrogenchloride; dmap; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; acetic acid; In pyridine; dichloromethane;
DOI:10.1016/j.carres.2006.04.006

Reference yield:

: 904690-70-6
2-(trimethylsilyl)ethyl 4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranoside

: 904690-73-9
2-(trimethylsilyl)ethyl 4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: AcOH / H₂O / 2 h / 65 °C

2: 141 g / camphorsulfonic acid / CH₂Cl₂ / 2 h / 22 °C

3: 82 percent / N-iodosuccinimide; TMSOTf / CH₂Cl₂ / 5 h / 0 - 22 °C

4: AcOH; aq. HCl / 0.33 h / 22 °C

5: 13.5 g / 4-dimethylaminopyridine / pyridine / 1 h / 22 °C

With hydrogenchloride; dmap; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; acetic acid; In pyridine; dichloromethane; water;
DOI:10.1016/j.carres.2006.04.006