1-O,2-O-Isopropylidene-3-O-methyl-alpha-D-glucofuranose

Base Information

• Chemical Name: 1-O,2-O-Isopropylidene-3-O-methyl-alpha-D-glucofuranose
• CAS No.: 43138-65-4
• Molecular Formula: C₁₀H₁₈O₆
• Molecular Weight: 234.249
• DSSTox Substance ID: DTXSID001206910
• Nikkaji Number: J1.152.527J
• Mol file: 43138-65-4.mol

Synonyms:SCHEMBL11656481;DTXSID001206910;1-O,2-O-Isopropylidene-3-O-methyl-alpha-D-glucofuranose;3-O-Methyl-1,2-O-(1-methylethylidene)-alpha-D-glucofuranose;43138-65-4

Chemical Property of 1-O,2-O-Isopropylidene-3-O-methyl-alpha-D-glucofuranose

Chemical Property:

• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 234.11033829
• Heavy Atom Count: 16
• Complexity: 256

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(OC2C(C(OC2O1)C(CO)O)OC)C
• Isomeric SMILES: CC1(O[C@@H]2[C@H]([C@H](O[C@@H]2O1)[C@@H](CO)O)OC)C

Technology Process of 1-O,2-O-Isopropylidene-3-O-methyl-alpha-D-glucofuranose

There total 1 articles about 1-O,2-O-Isopropylidene-3-O-methyl-alpha-D-glucofuranose 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:

1,2-O-isopropylidene-α-D-glucofuranose (18549-40-1) + methyl iodide (74-88-4) → methyl-5-O-methyl-1,2-O-(1-methylethylidene)-α-D-glucofuranose (5488-90-4) + 1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranose (43138-65-4)

Guidance literature:

With sodium methylate; Multistep reaction. Title compound not separated from byproducts; 1.) DMSO, MeOH, 20 deg C, 20 - 30 min; 2) 5 - 30 min;

DOI:10.1007/BF00962277

Reference yield: 100.0%

1-[6-methoxy-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro-[2,3-d][1,3]dioxol-5-yl]-(1R)-ethane-1,2-diol (18968-50-8,29587-02-8,32166-85-1,36215-54-0,43138-65-4,65725-74-8,67816-77-7) → 1,2-O-isopropylidene-3-O-methyl-α-D-ribo-pentodialdo-1,4-furanose (18968-51-9,43138-66-5,63522-21-4,816444-37-8)

Guidance literature:

With sodium periodate; In dichloromethane; at 0 - 20 ℃; for 6h;

DOI:10.1021/jo300865d

Reference yield: 98.0%

1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranose (43138-65-4) → 1,2-O-isopropylidene-3-O-methyl-α-D-xylo-pentodialdo-1,4-furanose (18968-51-9,43138-66-5,63522-21-4,816444-37-8)

Guidance literature:

With SiO₂-supported NaIO₄; In dichloromethane; at 20 ℃; for 2h;

upstream raw materials:

1,2-O-isopropylidene-α-D-glucofuranose

methyl iodide

Downstream raw materials:

1,2-O-isopropylidene-3-O-methyl-5,6-di-O-p-toluenesulfonyl-α-D-glucofuranose

5-O-Acetyl-1,2-O-isopropylidene-3-O-methyl-6-O-triphenylmethyl-α-D-glucopyranose

O⁵,O⁶-dibenzoyl-O¹,O²-isopropylidene-O³-methyl-α-D-glucofuranose

6-O-benzyl-1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranose