(2S,3R)-5-benzyl-2,3-O-isopropylidene-4-C-methylene-2-C-vinyl-D-erythro-pentitol

Base Information

• Chemical Name: (2S,3R)-5-benzyl-2,3-O-isopropylidene-4-C-methylene-2-C-vinyl-D-erythro-pentitol
• CAS No.: 328396-52-7
• Molecular Formula: C₁₈H₂₄O₄
• Molecular Weight: 304.386
• Mol file: 328396-52-7.mol

Synonyms:(2S,3R)-5-benzyl-2,3-O-isopropylidene-4-C-methylene-2-C-vinyl-D-erythro-pentitol

Chemical Property of (2S,3R)-5-benzyl-2,3-O-isopropylidene-4-C-methylene-2-C-vinyl-D-erythro-pentitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-5-benzyl-2,3-O-isopropylidene-4-C-methylene-2-C-vinyl-D-erythro-pentitol

There total 11 articles about (2S,3R)-5-benzyl-2,3-O-isopropylidene-4-C-methylene-2-C-vinyl-D-erythro-pentitol 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: 87.0%

vinyl magnesium bromide (1826-67-1) + (4R,5R)-5-(1-Benzyloxymethyl-vinyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde (495397-67-6) → (2S,3R)-5-benzyl-2,3-O-isopropylidene-4-C-methylene-2-C-vinyl-D-erythro-pentitol (328396-52-7)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1246/cl.2004.506

Reference yield:

(2S,3R)-5-benzyl-2,3-O-isopropylidene-4-C-methylene-D-erytho-pentitol (130114-57-7) → (2S,3R)-5-benzyl-2,3-O-isopropylidene-4-C-methylene-2-C-vinyl-D-erythro-pentitol (328396-52-7)

Guidance literature:

Multi-step reaction with 2 steps

1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2: 827.7 mg / tetrahydrofuran / 1 h / -78 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1: Swern oxidation;

DOI:10.1021/ol006999c

Reference yield:

1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-4-keto-D-erythro-pentitol (848862-73-7) → (2S,3R)-5-benzyl-2,3-O-isopropylidene-4-C-methylene-2-C-vinyl-D-erythro-pentitol (328396-52-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 93.4 percent / n-butyl lithium / tetrahydrofuran / 20 °C

2: 84.7 percent / n-tetrabutylammonium fluoride / acetonitrile / 2 h / 20 °C

3: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

4: 827.7 mg / tetrahydrofuran / 1 h / -78 °C

With n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; acetonitrile; 1: Wittig reaction / 3: Swern oxidation;

DOI:10.1021/ol006999c

upstream raw materials:

vinyl magnesium bromide

(4R,5R)-5-(1-Benzyloxymethyl-vinyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

2,3-O-isopropylidene-D-ribofuranose

D-Ribose

Downstream raw materials:

(3aR,6aR)-6-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-one

(4R,5S)-(-)-3-[(benzyloxy)methyl]-4,5-O-isopropylidene-2-cyclopenten-1-ol