methyl 2α-acetoxymethyl-3,5-di-O-(4-chlorobenzyl)-2-deoxy-α-D-ribofuranoside

Base Information

Chemical Name:methyl 2α-acetoxymethyl-3,5-di-O-(4-chlorobenzyl)-2-deoxy-α-D-ribofuranoside
CAS No.:733050-14-1
Molecular Formula:C₂₃H₂₆Cl₂O₆
Molecular Weight:469.362
Hs Code.:

Synonyms:methyl 2α-acetoxymethyl-3,5-di-O-(4-chlorobenzyl)-2-deoxy-α-D-ribofuranoside

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Chemical Property of methyl 2α-acetoxymethyl-3,5-di-O-(4-chlorobenzyl)-2-deoxy-α-D-ribofuranoside

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Technology Process of methyl 2α-acetoxymethyl-3,5-di-O-(4-chlorobenzyl)-2-deoxy-α-D-ribofuranoside

There total 4 articles about methyl 2α-acetoxymethyl-3,5-di-O-(4-chlorobenzyl)-2-deoxy-α-D-ribofuranoside 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: 98.0%

: 108-24-7
acetic anhydride

: 733050-13-0
methyl 3,5-di-O-(4-chlorobenzyl)-2-deoxy-2-α-(hydroxymethyl)-α-D-ribofuranoside

: 733050-14-1
methyl 2α-acetoxymethyl-3,5-di-O-(4-chlorobenzyl)-2-deoxy-α-D-ribofuranoside

Guidance literature:: With pyridine; dmap; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/jo0495337

Reference yield:

: 108008-66-8
methyl 3,5-di-O-(4-chlorobenzyl)-α-D-ribofuranoside

: 733050-14-1
methyl 2α-acetoxymethyl-3,5-di-O-(4-chlorobenzyl)-2-deoxy-α-D-ribofuranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

2.1: s-BuLi / cyclohexane; tetrahydrofuran / 1 h / -78 °C

2.2: 63 percent / cyclohexane; tetrahydrofuran / -78 - 20 °C

3.1: 9-BBN / tetrahydrofuran / 20 h / 20 °C

3.2: 84 percent / NaBO₃; H₂O / tetrahydrofuran / 3 h / 20 °C

4.1: 98 percent / pyridine; DMAP / CH₂Cl₂ / 2 h / 20 °C

With pyridine; dmap; 9-borabicyclo[3.3.1]nonane dimer; sec.-butyllithium; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; cyclohexane; 1.1: Dess-Martin oxidation;
DOI:10.1021/jo0495337

Reference yield:

: 733050-11-8
methyl 3,5-di-O-(4-chlorobenzyl)-2-keto-α-D-ribofuranoside

: 733050-14-1
methyl 2α-acetoxymethyl-3,5-di-O-(4-chlorobenzyl)-2-deoxy-α-D-ribofuranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: s-BuLi / cyclohexane; tetrahydrofuran / 1 h / -78 °C

1.2: 63 percent / cyclohexane; tetrahydrofuran / -78 - 20 °C

2.1: 9-BBN / tetrahydrofuran / 20 h / 20 °C

2.2: 84 percent / NaBO₃; H₂O / tetrahydrofuran / 3 h / 20 °C

3.1: 98 percent / pyridine; DMAP / CH₂Cl₂ / 2 h / 20 °C

With pyridine; dmap; 9-borabicyclo[3.3.1]nonane dimer; sec.-butyllithium; In tetrahydrofuran; dichloromethane; cyclohexane;
DOI:10.1021/jo0495337