(R)-N-[5-[[[6-O-benzoyl-4-O-(4,6-O-ethylidene-α-D-glucopyranosyl)-β-D-glucopyranosyl]oxy]methyl]-2-chlorophenyl]acetamide

Base Information

Chemical Name:(R)-N-[5-[[[6-O-benzoyl-4-O-(4,6-O-ethylidene-α-D-glucopyranosyl)-β-D-glucopyranosyl]oxy]methyl]-2-chlorophenyl]acetamide
CAS No.:269734-51-2
Molecular Formula:C₃₀H₃₆ClNO₁₃
Molecular Weight:654.068
Hs Code.:

Synonyms:(R)-N-[5-[[[6-O-benzoyl-4-O-(4,6-O-ethylidene-α-D-glucopyranosyl)-β-D-glucopyranosyl]oxy]methyl]-2-chlorophenyl]acetamide

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Chemical Property of (R)-N-[5-[[[6-O-benzoyl-4-O-(4,6-O-ethylidene-α-D-glucopyranosyl)-β-D-glucopyranosyl]oxy]methyl]-2-chlorophenyl]acetamide

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Technology Process of (R)-N-[5-[[[6-O-benzoyl-4-O-(4,6-O-ethylidene-α-D-glucopyranosyl)-β-D-glucopyranosyl]oxy]methyl]-2-chlorophenyl]acetamide

There total 7 articles about (R)-N-[5-[[[6-O-benzoyl-4-O-(4,6-O-ethylidene-α-D-glucopyranosyl)-β-D-glucopyranosyl]oxy]methyl]-2-chlorophenyl]acetamide 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: 54.0%

: N-{2-chloro-5-[(4',6'-O-ethylidene)-β-D-maltosyloxymethyl]phenyl}-acetamide

: 98-88-4
benzoyl chloride

: 269734-51-2
(R)-N-[5-[[[6-O-benzoyl-4-O-(4,6-O-ethylidene-α-D-glucopyranosyl)-β-D-glucopyranosyl]oxy]methyl]-2-chlorophenyl]acetamide

Guidance literature:: With 2,4,6-trimethyl-pyridine; In tetrahydrofuran; at -40 - 20 ℃; for 20h;

Reference yield: 54.0%

: 98-88-4
benzoyl chloride

: 721942-70-7
N-{2-Chloro-5-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl]-phenyl}-acetamide

: 269734-51-2
(R)-N-[5-[[[6-O-benzoyl-4-O-(4,6-O-ethylidene-α-D-glucopyranosyl)-β-D-glucopyranosyl]oxy]methyl]-2-chlorophenyl]acetamide

Guidance literature:: With 2,3,5-trimethyl-pyridine; In tetrahydrofuran; at -40 - 20 ℃;
DOI:10.1016/j.bmcl.2004.03.049

Reference yield:

: 55912-20-4
4-chloro-3-nitrobenzyl alcohol

: 269734-51-2
(R)-N-[5-[[[6-O-benzoyl-4-O-(4,6-O-ethylidene-α-D-glucopyranosyl)-β-D-glucopyranosyl]oxy]methyl]-2-chlorophenyl]acetamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: HgBr₂; Hg(CN)2 / acetonitrile / 0.5 h

1.2: 90 percent / acetonitrile / 18 h / 20 °C

2.1: 96 percent / tin(II) chloride dihydrate / ethyl acetate / 2 h / Heating

3.1: 75 percent / triethylamine / tetrahydrofuran / 6.5 h / 0 - 20 °C

4.1: 99 percent / NaOMe; MeOH / 2.5 h / Heating

5.1: 62 percent / TsOH*H₂O / dimethylformamide / 60 °C

6.1: 54 percent / collidine / tetrahydrofuran / -40 - 20 °C

With 2,3,5-trimethyl-pyridine; methanol; sodium methylate; mercury(II) cyanide; toluene-4-sulfonic acid; triethylamine; mercury dibromide; tin(ll) chloride; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.bmcl.2004.03.049