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

Base Information

• Chemical Name: (2S,3R)-5-benzyl-2,3-O-isopropylidene-4-C-methylene-D-erytho-pentitol
• CAS No.: 130114-57-7
• Molecular Formula: C₁₆H₂₂O₄
• Molecular Weight: 278.348
• Mol file: 130114-57-7.mol

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

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

There total 17 articles about (2S,3R)-5-benzyl-2,3-O-isopropylidene-4-C-methylene-D-erytho-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: 97.0%

1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-4-C-methylene-D-erythro-pentitol (848862-75-9) → (2S,3R)-5-benzyl-2,3-O-isopropylidene-4-C-methylene-D-erytho-pentitol (130114-57-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In acetonitrile; at 20 ℃; for 2h;

DOI:10.1016/j.tetasy.2004.11.069

Reference yield: 84.0%

1-O-benzyl-3,4-O-isopropylidene-L-ribulofuranose (130114-55-5,130114-56-6) + Methylenetriphenylphosphorane (19493-09-5) → (2S,3R)-5-benzyl-2,3-O-isopropylidene-4-C-methylene-D-erytho-pentitol (130114-57-7)

Guidance literature:

With (1,4,7,10-tetraoxacyclododecane); In tetrahydrofuran; for 4h; -60 deg C to r.t.;

DOI:10.1016/0040-4039(90)80222-8

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-D-erytho-pentitol (130114-57-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C

1.2: 92 percent / tetrahydrofuran; hexane / 16 h / 20 °C

2.1: 97 percent / tetrabutylammonium fluoride / acetonitrile / 2 h / 20 °C

With n-butyllithium; tetrabutyl ammonium fluoride; In tetrahydrofuran; hexane; acetonitrile;

DOI:10.1016/j.tetasy.2004.11.069

upstream raw materials:

1-O-benzyl-3,4-O-isopropylidene-L-ribulofuranose

Methylenetriphenylphosphorane

1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-4-C-methylene-D-erythro-pentitol

5-O-benzyl-2,3-O-isopropylidene-D-ribitol

Downstream raw materials:

(S)-((S)-2-Benzyloxymethyl-oxiranyl)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol

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

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

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