[(4'R,5'R)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]methyl benzoate

Base Information

• Chemical Name: [(4'R,5'R)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]methyl benzoate
• CAS No.: 1611459-83-6
• Molecular Formula: C₂₁H₂₄O₅
• Molecular Weight: 356.419
• Mol file: 1611459-83-6.mol

Synonyms:[(4'R,5'R)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]methyl benzoate

Chemical Property of [(4'R,5'R)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]methyl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(4'R,5'R)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]methyl benzoate

There total 7 articles about [(4'R,5'R)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]methyl benzoate 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: 91.0%

(2R,3R)-3-(benzyloxy)-2,4-dihydroxybutyl benzoate (1611459-80-3) + 2,2-dimethoxy-propane (77-76-9) → [(4'R,5'R)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]methyl benzoate (1611459-83-6)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.tetasy.2014.04.002

Reference yield:

C18H18O5 (1611459-82-5) → [(4'R,5'R)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]methyl benzoate (1611459-83-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate / methanol; dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

2: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere

With sodium tetrahydroborate; toluene-4-sulfonic acid; In methanol; dichloromethane;

DOI:10.1016/j.tetasy.2014.04.002

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose (34370-91-7,59358-33-7,68354-70-1,70798-12-8,19139-80-1) → [(4'R,5'R)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]methyl benzoate (1611459-83-6)

Guidance literature:

Multi-step reaction with 5 steps

1: dmap; pyridine / 1.67 h / 0 - 20 °C / Inert atmosphere

2: trifluoroacetic acid / water / 6 h / 0 °C / Inert atmosphere

3: sodium periodate / methanol; water / 1 h / 20 °C / Inert atmosphere

4: sodium tetrahydroborate / methanol; dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

5: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; toluene-4-sulfonic acid; trifluoroacetic acid; In methanol; dichloromethane; water;

DOI:10.1016/j.tetasy.2014.04.002

upstream raw materials:

C₁₈H₁₈O₅

(2R,3R)-3-(benzyloxy)-2,4-dihydroxybutyl benzoate

2,2-dimethoxy-propane

1,2-O-isopropylidene-3-O-benzyl-5-O-triphenylmethyl-α-D-xylofuranoside

Downstream raw materials:

(4R)-4-[(1'R,2'R)-2'-(benzyloxy)-1',3'-dihydroxypropyl]oxazolidin-2-one

(4R)-4-[(1'R,2'R)-2'-(benzyloxy)-1'-hydroxy-3'-(trityloxy)propyl]oxazolidin-2-one

(4R)-3-benzyl-4-[(1'R,2'R)-1',2'-bis(benzyloxy)-3'-(trityloxy)propyl]oxazolidin-2-one

N-{(1'R)-1'-[(4R,5R)-5-(benzyloxy)-2,2-dimethyl-1,3-dioxan-4-yl]-2'-hydroxyethyl}-2,2,2-trichloroacetamide