1,2-O-(1-methylethylidene)-3-deoxy-3-methylene-5-O-benzyl-L-xylofuranose

Base Information

• Chemical Name: 1,2-O-(1-methylethylidene)-3-deoxy-3-methylene-5-O-benzyl-L-xylofuranose
• CAS No.: 268750-13-6
• Molecular Formula: C₁₆H₂₀O₄
• Molecular Weight: 276.332
• Mol file: 268750-13-6.mol

Synonyms:1,2-O-(1-methylethylidene)-3-deoxy-3-methylene-5-O-benzyl-L-xylofuranose

Chemical Property of 1,2-O-(1-methylethylidene)-3-deoxy-3-methylene-5-O-benzyl-L-xylofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-O-(1-methylethylidene)-3-deoxy-3-methylene-5-O-benzyl-L-xylofuranose

There total 5 articles about 1,2-O-(1-methylethylidene)-3-deoxy-3-methylene-5-O-benzyl-L-xylofuranose 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: 71.0%

Methyltriphenylphosphonium bromide (1779-49-3) + (1R,3S,5S)-7,7-dimethyl-4,6,8-trioxa-3-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-one (155346-00-2) → 1,2-O-(1-methylethylidene)-3-deoxy-3-methylene-5-O-benzyl-L-xylofuranose (268750-13-6)

Guidance literature:

Methyltriphenylphosphonium bromide; With phenyllithium; In tetrahydrofuran; at -78 ℃; for 1h;

(1R,3S,5S)-7,7-dimethyl-4,6,8-trioxa-3-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-one; In tetrahydrofuran; at -78 - 55 ℃;

DOI:10.1080/15257770008033005

Reference yield:

L-xylopyranose (87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2) → 1,2-O-(1-methylethylidene)-3-deoxy-3-methylene-5-O-benzyl-L-xylofuranose (268750-13-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: CuSO₄; H₂SO₄ / acetone / 36 h / 20 °C

1.2: 98 percent / aq. HCl / H₂O / 6 h

2.1: 71 percent / pyridine / CHCl₃ / 20 °C

3.1: 85 percent / 17 h / 100 °C

4.1: 99 percent / dess-Martin periodinane / CH₂Cl₂ / 3.5 h / 20 °C

5.1: phenyl lithium / tetrahydrofuran / 1 h / -78 °C

5.2: 71 percent / tetrahydrofuran / -78 - 55 °C

With pyridine; sulfuric acid; Dess-Martin periodane; copper(II) sulfate; phenyllithium; In tetrahydrofuran; dichloromethane; chloroform; acetone; 1.1: Condensation / 1.2: Hydrolysis / 2.1: Tosylation / 3.1: Substitution / 4.1: Dess-Martin oxidation / 5.1: deprotonation / 5.2: Wittig reaction;

DOI:10.1080/15257770008033005

Reference yield:

1,2-O-isopropylidene-α-L-xylofuranose (114861-22-2) → 1,2-O-(1-methylethylidene)-3-deoxy-3-methylene-5-O-benzyl-L-xylofuranose (268750-13-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 71 percent / pyridine / CHCl₃ / 20 °C

2.1: 85 percent / 17 h / 100 °C

3.1: 99 percent / dess-Martin periodinane / CH₂Cl₂ / 3.5 h / 20 °C

4.1: phenyl lithium / tetrahydrofuran / 1 h / -78 °C

4.2: 71 percent / tetrahydrofuran / -78 - 55 °C

With pyridine; Dess-Martin periodane; phenyllithium; In tetrahydrofuran; dichloromethane; chloroform; 1.1: Tosylation / 2.1: Substitution / 3.1: Dess-Martin oxidation / 4.1: deprotonation / 4.2: Wittig reaction;

DOI:10.1080/15257770008033005

upstream raw materials:

Methyltriphenylphosphonium bromide

(1R,3S,5S)-7,7-dimethyl-4,6,8-trioxa-3-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-one

L-xylopyranose

1,2-O-isopropylidene-α-L-xylofuranose

Downstream raw materials:

1,2-O-(1-methylethylidene)-3-deoxy-3-(hydroxymethyl)-5-O-benzyl-L-ribofuranose