2,3-O-isopropylidene-2-C-methyl-D-erythritol 4-dibenzyl phosphate

Base Information

• Chemical Name: 2,3-O-isopropylidene-2-C-methyl-D-erythritol 4-dibenzyl phosphate
• CAS No.: 258518-31-9
• Molecular Formula: C₂₂H₂₉O₇P
• Molecular Weight: 436.442
• Mol file: 258518-31-9.mol

Synonyms:2,3-O-isopropylidene-2-C-methyl-D-erythritol 4-dibenzyl phosphate

Chemical Property of 2,3-O-isopropylidene-2-C-methyl-D-erythritol 4-dibenzyl phosphate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3-O-isopropylidene-2-C-methyl-D-erythritol 4-dibenzyl phosphate

There total 13 articles about 2,3-O-isopropylidene-2-C-methyl-D-erythritol 4-dibenzyl phosphate 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: 100.0%

2,3-O-isopropylidene-2-C-methyl-D-erythrose 4-dibenzyl phosphate (258518-30-8) → 2,3-O-isopropylidene-2-C-methyl-D-erythritol 4-dibenzyl phosphate (258518-31-9)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 - 25 ℃; for 2h;

DOI:10.1021/jo9905118

Reference yield: 96.0%

Phosphoric acid dibenzyl ester (4R,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2,5-trimethyl-[1,3]dioxolan-4-ylmethyl ester (931430-97-6) → 2,3-O-isopropylidene-2-C-methyl-D-erythritol 4-dibenzyl phosphate (258518-31-9)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at -10 - 25 ℃; for 3.25h;

DOI:10.1016/j.tet.2006.12.078

Reference yield:

2,3-O-isopropylidene-2-C-(p-toluenesulfonyloxymethyl)-D-erythrofuranose (931430-90-9) → 2,3-O-isopropylidene-2-C-methyl-D-erythritol 4-dibenzyl phosphate (258518-31-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 98 percent / LiAlH₄ / tetrahydrofuran / 10 h / Heating

2.1: NaH / tetrahydrofuran / 25 °C

2.2: tetrahydrofuran / 25 °C

3.1: 94 percent / imidazole / CH₂Cl₂ / 12 h / 25 °C

4.1: 93 percent / H₂ / Pd/C / methanol / 4 h / atmospheric pressure

5.1: I₂ / CH₂Cl₂ / 1 h / -10 - 25 °C

5.2: 92 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

6.1: 96 percent / TBAF; AcOH / tetrahydrofuran / 3.25 h / -10 - 25 °C

With 1H-imidazole; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium hydride; acetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/j.tet.2006.12.078

upstream raw materials:

2,3-O-isopropylidene-2-C-methyl-D-erythrose 4-dibenzyl phosphate

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

4-O-benzyl-2,3-O-isopropylidene-2-C-methyl-D-erythritol

1-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-2-C-methyl-D-erythritol

Downstream raw materials:

2-C-methyl-D-erythritol 4-phosphate