(4R,5S)-4,5-bis((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolane

Base Information

• Chemical Name: (4R,5S)-4,5-bis((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolane
• CAS No.: 71806-86-5
• Molecular Formula: C₂₁H₂₆O₄
• Molecular Weight: 342.435
• Mol file: 71806-86-5.mol

Synonyms:(4R,5S)-4,5-bis((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolane

Chemical Property of (4R,5S)-4,5-bis((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-4,5-bis((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolane

There total 7 articles about (4R,5S)-4,5-bis((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolane 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:

((4R,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol (55904-12-6) + benzyl bromide (100-39-0) → (4R,5S)-4,5-bis((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolane (71806-86-5)

Guidance literature:

((4R,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol; With sodium hydride; In tetrahydrofuran; paraffin oil; at 20 ℃; for 0.166667h; Inert atmosphere;

benzyl bromide; In tetrahydrofuran; paraffin oil; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/acs.joc.7b00992

Reference yield:

(1R,2R)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-1-(2-thiazolyl)-1,2,3-propanetriol (141873-73-6) → (4R,5S)-4,5-bis((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolane (71806-86-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

2: 1.) 60percent NaH / 1.) DMF, -15 deg C, 10 min., 2.) r.t., 2 h

With tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran;

DOI:10.1055/s-1992-34166

Reference yield:

(2R*,3S*)-1,4-bis(benzyloxy)butane-2,3-diol (69010-01-1) + 2,2-dimethoxy-propane (77-76-9) → (4R,5S)-4,5-bis((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolane (71806-86-5)

Guidance literature:

With toluene-4-sulfonic acid; at 35 ℃; for 2h;

DOI:10.1021/acs.joc.5b00544

upstream raw materials:

benzyl bromide

4-O-benzyl-2,3-O-isopropylidene-aldehydo-D-erythrose

(1R,2R)-1,2-O-isopropylidene-1-(2-thiazolyl)-1,2,3-propanetriol

(1R,2R)-3-O-benzyl-1,2-O-isopropylidene-1-(2-thiazolyl)-1,2,3-propanetriol

Downstream raw materials:

(2R*,3S*)-1,4-bis(benzyloxy)butane-2,3-diol

meso-2,3-O-isopropylidene-1,4-di-O-(methanesulfonyl)butane-1,2,3,4-tetrol