2-[(S)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-acrylic acid methyl ester

Base Information

• Chemical Name: 2-[(S)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-acrylic acid methyl ester
• CAS No.: 357625-77-5
• Molecular Formula: C₁₈H₂₄O₆
• Molecular Weight: 336.385
• Mol file: 357625-77-5.mol

Synonyms:2-[(S)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-acrylic acid methyl ester

Chemical Property of 2-[(S)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-acrylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(S)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-acrylic acid methyl ester

There total 1 articles about 2-[(S)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-acrylic acid methyl 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: 55.0%

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde (81028-12-8) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → 2-[(R)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-acrylic acid methyl ester + 2-[(S)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-acrylic acid methyl ester (357625-77-5)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; at 20 ℃; for 48h; Inert atmosphere;

DOI:10.1002/ejoc.200900772

Reference yield:

2-[(S)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-acrylic acid methyl ester (357625-77-5) → (2S,3R)-3-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,3-dihydroxy-2-hydroxymethyl-propionic acid methyl ester (1053628-43-5)

Guidance literature:

With osmium(VIII) oxide; N-methyl-2-indolinone; In acetone; at 20 ℃;

Reference yield:

2-[(S)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-acrylic acid methyl ester (357625-77-5) → (S)-1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-propane-1,2,3-triol

Guidance literature:

Multi-step reaction with 6 steps

1: aq. OsO₄; NMO / acetone / 20 °C

2: Et₃N; DMAP

3: pyridine / CH₂Cl₂ / 0 - 20 °C

4: K₂CO₃ / methanol / 20 °C

5: DIBAL-H / CH₂Cl₂ / -78 °C

6: NaBH₄ / methanol / 0 °C

With pyridine; dmap; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; diisobutylaluminium hydride; potassium carbonate; triethylamine; In methanol; dichloromethane; acetone;

upstream raw materials:

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde

acrylic acid methyl ester

Downstream raw materials:

(2S,3R)-3-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,3-dihydroxy-2-hydroxymethyl-propionic acid methyl ester

(2S,3S)-3-((4R,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-oxirane-2-carboxylic acid methyl ester

[(2S,3S)-3-((4R,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-oxiranyl]-methanol

(2S,3R)-3-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydroxy-propionic acid methyl ester