(4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-N-(phenylmethoxy)-1,3-dioxolane-4-carboxamide

Base Information

• Chemical Name: (4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-N-(phenylmethoxy)-1,3-dioxolane-4-carboxamide
• CAS No.: 717920-96-2
• Molecular Formula: C₁₄H₁₉NO₅
• Molecular Weight: 281.309
• Mol file: 717920-96-2.mol

Synonyms:(4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-N-(phenylmethoxy)-1,3-dioxolane-4-carboxamide

Chemical Property of (4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-N-(phenylmethoxy)-1,3-dioxolane-4-carboxamide

Chemical Property:

Purity/Quality:

99%+ ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-N-(phenylmethoxy)-1,3-dioxolane-4-carboxamide

There total 2 articles about (4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-N-(phenylmethoxy)-1,3-dioxolane-4-carboxamide 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: 66.0%

D-erythronolactone acetonide (25581-41-3) + N-benzyl hydroxylalmine (622-30-0) → (4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-N-(phenylmethoxy)-1,3-dioxolane-4-carboxamide (717920-96-2)

Guidance literature:

D-erythronolactone acetonide; N-benzyl hydroxylalmine; In dichloromethane; at 25 ℃; for 0.5h;

With trimethylaluminum; In hexane; dichloromethane; at 25 ℃; for 3.33333h; Cooling with ice;

DOI:10.1016/j.bmcl.2010.12.066

Reference yield: 56.0%

D-erythronolactone acetonide (25581-41-3) + O-benzylhydoxylamine hydrochloride (2687-43-6) → (4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-N-(phenylmethoxy)-1,3-dioxolane-4-carboxamide (717920-96-2)

Guidance literature:

O-benzylhydoxylamine hydrochloride; With sodium methylate; In methanol; at 0 ℃; for 1h;

D-erythronolactone acetonide; In dichloromethane; at 20 ℃; for 0.5h;

With trimethylaluminum; In hexane; dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1021/jm031066i

Reference yield: 73.0%

dibenzyl phosphoroiodidate (176506-97-1) + (4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-N-(phenylmethoxy)-1,3-dioxolane-4-carboxamide (717920-96-2) → Phosphoric acid dibenzyl ester (4R,5R)-5-benzyloxycarbamoyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (717920-97-3)

Guidance literature:

With pyridine; In dichloromethane; at -78 ℃; for 1.5h;

DOI:10.1021/jm031066i

upstream raw materials:

D-erythronolactone acetonide

O-benzylhydoxylamine hydrochloride

N-benzyl hydroxylalmine

Downstream raw materials:

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

Phosphoric acid dibenzyl ester (2R,3R)-3-benzyloxycarbamoyl-2,3-dihydroxy-propyl ester

Acetic acid (1R,2R)-2-acetoxy-2-benzyloxycarbamoyl-1-(bis-benzyloxy-phosphoryloxymethyl)-ethyl ester

[(4R,5R)-2,2-dimethyl-5-[[(phenylmethoxy)amino]carbonyl]-1,3-dioxolan-4-yl]methylphosphoric acid, bis(phenylmethyl) ester