(1S)-1-{(4S,5S)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethane-1,2-diol

Base Information

Chemical Name:(1S)-1-{(4S,5S)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethane-1,2-diol
CAS No.:1308324-56-2
Molecular Formula:C₁₅H₂₂O₅
Molecular Weight:282.337
Hs Code.:

Synonyms:(1S)-1-{(4S,5S)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethane-1,2-diol

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Chemical Property of (1S)-1-{(4S,5S)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethane-1,2-diol

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Technology Process of (1S)-1-{(4S,5S)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethane-1,2-diol

There total 2 articles about (1S)-1-{(4S,5S)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethane-1,2-diol 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%

: 143878-62-0
(4S,5S)-4-[(benzyloxy)methyl]-2,2-dimethyl-5-vinyl-1,3-dioxolane

: (1R)-1-{(4S,5S)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethane-1,2-diol

: 1308324-56-2
(1S)-1-{(4S,5S)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethane-1,2-diol

Guidance literature:: With osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; In acetone; at 20 ℃; for 48h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tetasy.2011.02.010

Reference yield:

: 81028-12-8
(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde

: 1308324-56-2
(1S)-1-{(4S,5S)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethane-1,2-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 - 20 °C / Inert atmosphere

1.2: 0.75 h / -78 °C / Inert atmosphere

2.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone / 48 h / 20 °C / Inert atmosphere

With osmium(VIII) oxide; n-butyllithium; water; 4-methylmorpholine N-oxide; In tetrahydrofuran; hexane; acetone;
DOI:10.1016/j.tetasy.2011.02.010

Reference yield: 90.0%

: 1308324-56-2
(1S)-1-{(4S,5S)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethane-1,2-diol

: 98-59-9
p-toluenesulfonyl chloride

: 1308324-57-3
C₂₂H₂₈O₇S

Guidance literature:: With dmap; di(n-butyl)tin oxide; triethylamine; In dichloromethane; at 0 - 20 ℃; for 1h; regioselective reaction; Inert atmosphere;
DOI:10.1016/j.tetasy.2011.02.010