(2S,3R)-methyl 5-(bis-benzyloxyphosphoryloxymethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylate

Base Information

• Chemical Name: (2S,3R)-methyl 5-(bis-benzyloxyphosphoryloxymethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylate
• CAS No.: 798554-50-4
• Molecular Formula: C₂₂H₂₇O₈P
• Molecular Weight: 450.425
• Mol file: 798554-50-4.mol

Synonyms:(2S,3R)-methyl 5-(bis-benzyloxyphosphoryloxymethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylate

Chemical Property of (2S,3R)-methyl 5-(bis-benzyloxyphosphoryloxymethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-methyl 5-(bis-benzyloxyphosphoryloxymethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylate

There total 8 articles about (2S,3R)-methyl 5-(bis-benzyloxyphosphoryloxymethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylate 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: 86.0%

(4S,5R)-methyl 5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate (28762-00-7) + tribenzyl phosphite (15205-57-9) → (2S,3R)-methyl 5-(bis-benzyloxyphosphoryloxymethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylate (798554-50-4)

Guidance literature:

With pyridine; iodine; In dichloromethane; at -40 - 20 ℃;

DOI:10.1021/jo048022h

Reference yield: 79.0%

(4S,5R)-methyl 5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate (28762-00-7) + dibenzyl phosphoroiodidate (176506-97-1) → (2S,3R)-methyl 5-(bis-benzyloxyphosphoryloxymethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylate (798554-50-4)

Guidance literature:

With pyridine; In dichloromethane; at -30 - 20 ℃; for 4h;

DOI:10.1021/jo0516786

Reference yield:

(+)-dimethyl-2,3-O-isopropylidene-D-tartrate (37031-29-1,6134-82-3,6135-80-4,90613-41-5,116499-08-2,37031-30-4) → (2S,3R)-methyl 5-(bis-benzyloxyphosphoryloxymethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylate (798554-50-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 32 percent / NaBH₄ / methanol / 0.5 h / 0 °C

2: 79 percent / pyridine / CH₂Cl₂ / 4 h / -30 - 20 °C

With pyridine; sodium tetrahydroborate; In methanol; dichloromethane;

DOI:10.1021/jo0516786

upstream raw materials:

methanol

Phosphoric acid dibenzyl ester (4R,5S)-5-formyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

(4S,5R)-methyl 5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate

tribenzyl phosphite

Downstream raw materials:

dibenzyl (2S,3R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl phosphate

dibenzyl (2S,3R)-5-hydroxycarbamoyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl phosphate

(2S,3R)-5-(bis-benzyloxyphosphoryloxymethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid

dibenzyl (2S,3R)-5-carbamoyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl phosphate