α-L-Xylofuranose,1,2:3,5-bis-O-(1-Methylethylidene)-

Base Information

• Chemical Name: α-L-Xylofuranose,1,2:3,5-bis-O-(1-Methylethylidene)-
• CAS No.: 131156-47-3
• Molecular Formula: C11H18O5
• Molecular Weight: 230.261
• Mol file: 131156-47-3.mol

Synonyms:α-L-Xylofuranose,1,2:3,5-bis-O-(1-Methylethylidene)-;1,2:3,5-DI-O-ISOPROPYLIDENE-ALPHA-L-XYLOFURANOSE;(-)-1,2:3,5-di-O-isopropylidene-α-L-xylofuranose;(3aS,3bR,7aS,8aS)-2,2,5,5-tetramethyltetrahydro-3aH-[1,3]dioxolo[4',5':4,5]furo[3,2-d][1,3]dioxine

Chemical Property of α-L-Xylofuranose,1,2:3,5-bis-O-(1-Methylethylidene)-

Chemical Property:

• Melting Point: 39-40 °C
• Boiling Point: 272.2±35.0 °C(Predicted)
• PSA: 46.15000
• Density: 1.112±0.06 g/cm3(Predicted)
• LogP: 1.01430
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

(3AS,3bR,7aS,8aS)-2,2,5,5-tetramethyltetrahydro-3aH-[1,3]dioxolo[4',5':4,5]furo[3,2-d][1,3]dioxine 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of α-L-Xylofuranose,1,2:3,5-bis-O-(1-Methylethylidene)-

There total 19 articles about α-L-Xylofuranose,1,2:3,5-bis-O-(1-Methylethylidene)- 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: 95.0%

L-xylose (609-06-3) + acetone (67-64-1) → (3aS,3bR,7aS,8aS)-2,2,5,5-tetramethyltetrahydro-3aH-[1,3]dioxolo[4',5':4,5]furo[3,2-d][1,3]dioxane (131156-47-3)

Guidance literature:

With malonic acid; choline chloride; for 0.666667h; Inert atmosphere; Reflux;

Reference yield: 85.0%

D-xylose (58-86-6) + acetone (67-64-1) → (3aS,3bR,7aS,8aS)-2,2,5,5-tetramethyltetrahydro-3aH-[1,3]dioxolo[4',5':4,5]furo[3,2-d][1,3]dioxane (131156-47-3)

Guidance literature:

With sulfonated polystyrene cation exchange resin CAT₆₀₀; at 40 ℃; for 3h; Green chemistry;

DOI:10.5012/bkcs.2014.35.7.2165

Reference yield: 85.0%

L-xylose (41546-31-0) + acetone (67-64-1) → (3aS,3bR,7aS,8aS)-2,2,5,5-tetramethyltetrahydro-3aH-[1,3]dioxolo[4',5':4,5]furo[3,2-d][1,3]dioxane (131156-47-3)

Guidance literature:

With sulfuric acid; copper(II) sulfate; at 20 ℃; for 24h;

DOI:10.1039/c6ra02792j

upstream raw materials:

L-xylose

2,3:4,6-di-O-isopropylidene-2-keto-L-gulonyl chloride

L-(-)-xylose

acetone

Downstream raw materials:

1,2-O-isopropylidene-α-L-xylofuranose

5-O-benzoyl-1,2-O-isopropylidene-7α-L-xylofuranose

(3aS,5R,6R,6aS)-6-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde

5-O-benzoyl-3-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-L-xylofuranose

Refernces

• 1、 Zhao, Matthew M.,Zhang, Haiming,Iimura, Shinya,Bednarz, Mark S.,Song, Qiu-Ling,Lim, Ngiap-Kie,Yan, Jie,Wu, Wenxue,Dai, Kuangchu,Gu, Xiaodong,Wang, Youchu. "Process development of sotagliflozin, a dual inhibitor of sodium- Glucose cotransporter-1/2 for the treatment of diabetes". . p. 2689 - 2701. Retrieved 2020/11/03.
• 2、 Patpi, Santhosh Reddy,Jin, Guangyi,Kantevari, Srinivas. "Total Synthesis of 5-Hydroxygoniothalamin". . p. 780 - 786. Retrieved 2019/01/23.