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

Base Information

Chemical Name:methyl 3,5-di-O-(4-chlorobenzyl)-2-deoxy-2-α-(hydroxymethyl)-α-D-ribofuranoside
CAS No.:733050-13-0
Molecular Formula:C₂₁H₂₄Cl₂O₅
Molecular Weight:427.325
Hs Code.:

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

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

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

There total 6 articles about methyl 3,5-di-O-(4-chlorobenzyl)-2-deoxy-2-α-(hydroxymethyl)-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: 87.0%

: 733050-12-9
methyl-3,5-di-O-(4-chlorobenzyl)-2-deoxy-2-methylene-β-D-ribofuranoside

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

Guidance literature:: methyl-3,5-di-O-(4-chlorobenzyl)-2-deoxy-2-methylene-β-D-ribofuranoside; With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; Further stages.;
DOI:10.1080/15257770701542199

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 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

With 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

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

Guidance literature:: Multi-step reaction with 2 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

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