tert-butyl 2-chloro-5-(1-methoxy-2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)benzoate

Base Information

Chemical Name:tert-butyl 2-chloro-5-(1-methoxy-2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)benzoate
CAS No.:842134-04-7
Molecular Formula:C₂₆H₃₃ClO₁₂
Molecular Weight:572.994
Hs Code.:

Synonyms:tert-butyl 2-chloro-5-(1-methoxy-2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)benzoate

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Chemical Property of tert-butyl 2-chloro-5-(1-methoxy-2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)benzoate

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Technology Process of tert-butyl 2-chloro-5-(1-methoxy-2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)benzoate

There total 4 articles about tert-butyl 2-chloro-5-(1-methoxy-2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)benzoate 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:

: 842134-03-6
tert-butyl 2-chloro-5-(1-methoxy-D-glucopyranosyl)benzoate

: 108-24-7
acetic anhydride

: 842134-04-7
tert-butyl 2-chloro-5-(1-methoxy-2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)benzoate

Guidance literature:: With dmap; N-ethyl-N,N-diisopropylamine; In toluene; at 0 - 20 ℃; for 1h;
DOI:10.1016/j.bmc.2013.05.048

Reference yield:

: 32469-28-6,55515-28-1,55515-29-2,32384-65-9
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

: 842134-04-7
tert-butyl 2-chloro-5-(1-methoxy-2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)benzoate

Guidance literature:: Multi-step reaction with 3 steps

1: mesityllithium / hexane; tetrahydrofuran / 1.5 h / -78 - -63 °C / Inert atmosphere

2: methanesulfonic acid / hexane; tetrahydrofuran / 40.08 h / -78 - 20 °C / Inert atmosphere

3: dmap; N-ethyl-N,N-diisopropylamine / toluene / 1 h / 0 - 20 °C

With dmap; methanesulfonic acid; mesityllithium; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; toluene; 1: |Barbier Coupling Reaction;
DOI:10.1016/j.bmc.2013.05.048

Reference yield:

: C₂₉H₅₅ClO₈Si₄

: 842134-04-7
tert-butyl 2-chloro-5-(1-methoxy-2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)benzoate

Guidance literature:: Multi-step reaction with 2 steps

1: methanesulfonic acid / hexane; tetrahydrofuran / 40.08 h / -78 - 20 °C / Inert atmosphere

2: dmap; N-ethyl-N,N-diisopropylamine / toluene / 1 h / 0 - 20 °C

With dmap; methanesulfonic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; toluene;
DOI:10.1016/j.bmc.2013.05.048