benzyl 2-deoxy-3,4-O-isopropylidene-2-methylene-β-L-erythro-pentopyranoside

Base Information

• Chemical Name: benzyl 2-deoxy-3,4-O-isopropylidene-2-methylene-β-L-erythro-pentopyranoside
• CAS No.: 123490-19-7
• Molecular Formula: C₁₆H₂₀O₄
• Molecular Weight: 276.332
• Mol file: 123490-19-7.mol

Synonyms:benzyl 2-deoxy-3,4-O-isopropylidene-2-methylene-β-L-erythro-pentopyranoside

Chemical Property of benzyl 2-deoxy-3,4-O-isopropylidene-2-methylene-β-L-erythro-pentopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2-deoxy-3,4-O-isopropylidene-2-methylene-β-L-erythro-pentopyranoside

There total 6 articles about benzyl 2-deoxy-3,4-O-isopropylidene-2-methylene-β-L-erythro-pentopyranoside 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: 80.0%

benzyl 3,4-O-(1-methylethylidene)-β-L-erythro-pent-2-ulosylpyranoside (65247-32-7) + Methylenetriphenylphosphorane (19493-09-5) → benzyl 2-deoxy-3,4-O-isopropylidene-2-methylene-β-L-erythro-pentopyranoside (123490-19-7)

Guidance literature:

DOI:10.1016/S0040-4039(01)80275-6

Reference yield:

(3aS,6S,7R,7aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol (18403-22-0) → benzyl 2-deoxy-3,4-O-isopropylidene-2-methylene-β-L-erythro-pentopyranoside (123490-19-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: TEMPO; NaOCl; NaHCO₃ / NaBr / CH₂Cl₂; H₂O / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: 10.1 g / tetrahydrofuran / 19 h / -78 - 20 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; n-butyllithium; sodium hydrogencarbonate; sodium bromide; In tetrahydrofuran; hexane; dichloromethane; water;

DOI:10.1039/b103756k

Reference yield:

benzyl 3,4-O-(1-methylethylidene)-β-L-erythro-pent-2-ulosylpyranoside (65247-32-7) + methyl-triphenylphosphonium iodide (2065-66-9) → benzyl 2-deoxy-3,4-O-isopropylidene-2-methylene-β-L-erythro-pentopyranoside (123490-19-7)

Guidance literature:

methyl-triphenylphosphonium iodide; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

benzyl 3,4-O-(1-methylethylidene)-β-L-erythro-pent-2-ulosylpyranoside; In tetrahydrofuran; at -78 - 20 ℃; for 19h; Further stages.;

DOI:10.1039/b103756k

upstream raw materials:

benzyl 3,4-O-(1-methylethylidene)-β-L-erythro-pent-2-ulosylpyranoside

Methylenetriphenylphosphorane

methyl-triphenylphosphonium iodide

(3aS,6S,7R,7aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol

Downstream raw materials:

C₁₇H₂₀Cl₂O₄

C₁₇H₂₀Cl₂O₄

benzyl 2-deoxy-3,4-O-isopropylidene-2-C-methyl-β-L-ribopyranoside

(3S,4R,5R)-1-[(3R,4S,5R)-1-benzyloxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidenepiperidine-3-carbonyl]-3,4-isopropylidenedioxy-5-methylpiperidine