(3β,18β,20β)-3-N-{2-[methyl (2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranosyl)uronate]ethylacetylamino}-3-deoxy-11-oxo-olean-12-en-29-oic acid diphenylmethyl ester

Base Information

Chemical Name:(3β,18β,20β)-3-N-{2-[methyl (2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranosyl)uronate]ethylacetylamino}-3-deoxy-11-oxo-olean-12-en-29-oic acid diphenylmethyl ester
CAS No.:1257409-39-4
Molecular Formula:C₆₀H₇₉NO₁₃S
Molecular Weight:1054.35
Hs Code.:

(3β,18β,20β)-3-N-{2-[methyl (2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranosyl)uronate]ethylacetylamino}-3-deoxy-11-oxo-olean-12-en-29-oic acid diphenylmethyl ester

Synonyms:(3β,18β,20β)-3-N-{2-[methyl (2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranosyl)uronate]ethylacetylamino}-3-deoxy-11-oxo-olean-12-en-29-oic acid diphenylmethyl ester

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Chemical Property of (3β,18β,20β)-3-N-{2-[methyl (2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranosyl)uronate]ethylacetylamino}-3-deoxy-11-oxo-olean-12-en-29-oic acid diphenylmethyl ester

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Technology Process of (3β,18β,20β)-3-N-{2-[methyl (2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranosyl)uronate]ethylacetylamino}-3-deoxy-11-oxo-olean-12-en-29-oic acid diphenylmethyl ester

There total 7 articles about (3β,18β,20β)-3-N-{2-[methyl (2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranosyl)uronate]ethylacetylamino}-3-deoxy-11-oxo-olean-12-en-29-oic acid diphenylmethyl ester 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: 95.6%

: 1257409-37-2
(3β,18β,20β)-3-{2-[methyl (2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranosyl)uronate]ethylamino}-11-oxo-olean-12-en-29-oic acid diphenylmethyl ester

: 108-24-7
acetic anhydride

: 1257409-39-4
(3β,18β,20β)-3-N-{2-[methyl (2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranosyl)uronate]ethylacetylamino}-3-deoxy-11-oxo-olean-12-en-29-oic acid diphenylmethyl ester

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 2h; Inert atmosphere;
DOI:10.3762/bjoc.8.79

Reference yield:

: 1257409-36-1
methyl (1-O-(2-iodoethyl)-2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranosyl)uronate

: 1257409-39-4
(3β,18β,20β)-3-N-{2-[methyl (2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranosyl)uronate]ethylacetylamino}-3-deoxy-11-oxo-olean-12-en-29-oic acid diphenylmethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 45 - 50 °C / Inert atmosphere

2: triethylamine / dichloromethane / 2 h / 0 °C / Inert atmosphere

With triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.3762/bjoc.8.79

Reference yield:

: 68354-87-0
1-Thio-1-desoxy-(2,3,4-tri-O-acetyl-β-D-glucuronsaeuremethylester)

: 1257409-39-4
(3β,18β,20β)-3-N-{2-[methyl (2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranosyl)uronate]ethylacetylamino}-3-deoxy-11-oxo-olean-12-en-29-oic acid diphenylmethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: sodium hydride / hexane; N,N-dimethyl-formamide / -5 °C / Inert atmosphere

2: sodium iodide / acetone / 16 h / 4 °C / Inert atmosphere; Darkness

3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 45 - 50 °C / Inert atmosphere

4: triethylamine / dichloromethane / 2 h / 0 °C / Inert atmosphere

With sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; In hexane; dichloromethane; N,N-dimethyl-formamide; acetone; 2: Finkelstein reaction;
DOI:10.3762/bjoc.8.79