4-methoxyphenyl 2-(acetylamino)-3,4-di-O-benzoyl-2-deoxy-6-O-[3,4-O-(1-methylethylidene)-α-L-arabinopyranosyl]-β-D-glucopyranoside

Base Information

Chemical Name:4-methoxyphenyl 2-(acetylamino)-3,4-di-O-benzoyl-2-deoxy-6-O-[3,4-O-(1-methylethylidene)-α-L-arabinopyranosyl]-β-D-glucopyranoside
CAS No.:1603837-22-4
Molecular Formula:C₃₇H₄₁NO₁₃
Molecular Weight:707.731
Hs Code.:

Synonyms:4-methoxyphenyl 2-(acetylamino)-3,4-di-O-benzoyl-2-deoxy-6-O-[3,4-O-(1-methylethylidene)-α-L-arabinopyranosyl]-β-D-glucopyranoside

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Chemical Property of 4-methoxyphenyl 2-(acetylamino)-3,4-di-O-benzoyl-2-deoxy-6-O-[3,4-O-(1-methylethylidene)-α-L-arabinopyranosyl]-β-D-glucopyranoside

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Technology Process of 4-methoxyphenyl 2-(acetylamino)-3,4-di-O-benzoyl-2-deoxy-6-O-[3,4-O-(1-methylethylidene)-α-L-arabinopyranosyl]-β-D-glucopyranoside

There total 9 articles about 4-methoxyphenyl 2-(acetylamino)-3,4-di-O-benzoyl-2-deoxy-6-O-[3,4-O-(1-methylethylidene)-α-L-arabinopyranosyl]-β-D-glucopyranoside 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: 90.0%

: 1603837-21-3
4-methoxyphenyl 2-(acetylamino)-6-O-[2-O-acetyl-3,4-O-(1-methylethylidene)-α-L-arabinopyranosyl]-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranoside

: 1603837-22-4
4-methoxyphenyl 2-(acetylamino)-3,4-di-O-benzoyl-2-deoxy-6-O-[3,4-O-(1-methylethylidene)-α-L-arabinopyranosyl]-β-D-glucopyranoside

Guidance literature:: With acetyl chloride; In methanol; dichloromethane; at 20 ℃;
DOI:10.1002/hlca.201300195

Reference yield:

: 3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3,14086-90-9
2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate

: 1603837-22-4
4-methoxyphenyl 2-(acetylamino)-3,4-di-O-benzoyl-2-deoxy-6-O-[3,4-O-(1-methylethylidene)-α-L-arabinopyranosyl]-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / 7 h / -30 - 20 °C

2.1: sodium methylate / methanol / 0.5 h / 20 °C

3.1: pyridine / 6 h / 20 °C

4.1: 5 h / 20 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

6.1: dichloromethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

6.2: 1 h / 0 °C / Molecular sieve; Inert atmosphere

7.1: acetyl chloride / methanol; dichloromethane / 20 °C

With pyridine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; acetyl chloride; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1002/hlca.201300195

Reference yield:

: p-tolyl 1-thio-α-L-arabinopyranoside

: 1603837-22-4
4-methoxyphenyl 2-(acetylamino)-3,4-di-O-benzoyl-2-deoxy-6-O-[3,4-O-(1-methylethylidene)-α-L-arabinopyranosyl]-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: camphor-10-sulfonic acid / N,N-dimethyl-formamide / 5 h / 50 °C

2.1: triethylamine; dmap / dichloromethane / 1.5 h / 20 °C

3.1: dichloromethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

3.2: 1 h / 0 °C / Molecular sieve; Inert atmosphere

4.1: acetyl chloride / methanol; dichloromethane / 20 °C

With dmap; camphor-10-sulfonic acid; triethylamine; acetyl chloride; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/hlca.201300195