Phosphoric acid, [(4R,5S)-5-[(methoxymethylamino)carbonyl]-2,2-dimethyl-1,3-dioxolan- 4-yl]methyl bis(phenylmethyl) ester

Base Information

• Chemical Name: Phosphoric acid, [(4R,5S)-5-[(methoxymethylamino)carbonyl]-2,2-dimethyl-1,3-dioxolan- 4-yl]methyl bis(phenylmethyl) ester
• CAS No.: 850144-25-1
• Molecular Formula: C23H30NO8P
• Molecular Weight: 479.467
• Mol file: 850144-25-1.mol

Synonyms:

Chemical Property of Phosphoric acid, [(4R,5S)-5-[(methoxymethylamino)carbonyl]-2,2-dimethyl-1,3-dioxolan- 4-yl]methyl bis(phenylmethyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phosphoric acid, [(4R,5S)-5-[(methoxymethylamino)carbonyl]-2,2-dimethyl-1,3-dioxolan- 4-yl]methyl bis(phenylmethyl) ester

There total 2 articles about Phosphoric acid, [(4R,5S)-5-[(methoxymethylamino)carbonyl]-2,2-dimethyl-1,3-dioxolan- 4-yl]methyl bis(phenylmethyl) ester 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:

(4S,5R)-methyl 5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate (28762-00-7) → dibenzyl [(2S,3R)-2,3-(isopropylidenedioxy)-N-methoxy-N-methylbutanamid-4-yl] phosphate (850144-25-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / CH₃MgBr / tetrahydrofuran / 2 h / -20 °C

2: 80 percent / I₂; pyridine / CH₂Cl₂ / -40 - 20 °C

With pyridine; methylmagnesium bromide; iodine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo048022h

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) → dibenzyl [(2S,3R)-2,3-(isopropylidenedioxy)-N-methoxy-N-methylbutanamid-4-yl] phosphate (850144-25-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 31 percent / NaNH₄ / methanol / 1 h / 0 °C

2: 60 percent / CH₃MgBr / tetrahydrofuran / 2 h / -20 °C

3: 80 percent / I₂; pyridine / CH₂Cl₂ / -40 - 20 °C

With pyridine; methylmagnesium bromide; iodine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo048022h

Reference yield: 85.0%

ethylmagnesium bromide (925-90-6) + dibenzyl [(2S,3R)-2,3-(isopropylidenedioxy)-N-methoxy-N-methylbutanamid-4-yl] phosphate (850144-25-1) → dibenzyl (4S,5R)-3-oxo-4,5-(isopropylidenedioxy)hexan-6-yl phosphate (850144-26-2)

Guidance literature:

In diethyl ether; at -40 ℃; for 1h;

DOI:10.1021/jo048022h

upstream raw materials:

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

(+)-dimethyl-2,3-O-isopropylidene-D-tartrate

Downstream raw materials:

dibenzyl (4S,5R)-3-oxo-4,5-(isopropylidenedioxy)hexan-6-yl phosphate