4-(hydroxymethyl)-6-methoxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol

Base Information

• Chemical Name: 4-(hydroxymethyl)-6-methoxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol
• CAS No.: 40269-01-0
• Molecular Formula: C10H18O6
• Molecular Weight: 234.249
• NSC Number: 170242
• DSSTox Substance ID: DTXSID90960664
• Mol file: 40269-01-0.mol

Synonyms:40269-01-0;4-(hydroxymethyl)-6-methoxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol;methyl 3,4-O-(1-methylethylidene)hexopyranoside;Methyl3,4-O-Isopropylidene-alpha-D-galactopyranoside;NSC170242;DTXSID90960664;NSC-170242;FT-0671869

Chemical Property of 4-(hydroxymethyl)-6-methoxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol

Chemical Property:

• Vapor Pressure: 1.93E-07mmHg at 25°C
• Boiling Point: 382.9°C at 760 mmHg
• Flash Point: 185.4°C
• PSA: 77.38000
• Density: 1.3g/cm³
• LogP: -0.76900
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 234.11033829
• Heavy Atom Count: 16
• Complexity: 256

Purity/Quality:

99%min ^*data from raw suppliers

Methyl3,4-O-Isopropylidene-α-D-galactopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(OC(C(C2O1)O)OC)CO)C
• Uses: Methyl 3,4-O-Isopropylidene-α-D-galactopyranoside (cas# 40269-01-0) is a compound useful in organic synthesis.

Technology Process of 4-(hydroxymethyl)-6-methoxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol

There total 17 articles about 4-(hydroxymethyl)-6-methoxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol 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%

acetone (67-64-1) + methyl α-D-galactopyranoside (3396-99-4) → methyl 3,4-O-isopropylidene-α-D-galactopyranoside (40269-01-0)

Guidance literature:

With nano n-propylsulfonated magnetic γ-Fe₂O₃; for 1.5h; Reflux;

DOI:10.1080/07328303.2013.804082

Reference yield: 91.0%

2,2-dimethoxy-propane (77-76-9) + methyl α-D-galactopyranoside (3396-99-4) → methyl 3,4-O-isopropylidene-α-D-galactopyranoside (40269-01-0)

Guidance literature:

With toluene-4-sulfonic acid; for 48h; Ambient temperature;

Reference yield: 87.0%

2-Methoxypropene (116-11-0) + methyl α-D-galactopyranoside (3396-99-4) → methyl 3,4-O-isopropylidene-α-D-galactopyranoside (40269-01-0)

Guidance literature:

vanadyl triflate; In acetonitrile; at 20 ℃; for 6h;

DOI:10.1016/j.carres.2006.04.001

upstream raw materials:

methyl α-D-galactopyranoside

Methyl 3,4-O-isopropylidene-2,6-di-O-(1-methoxy-1-methylethyl)-α-D-galactopyranoside

Methyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-α-D-galactopyranoside

2,2-dimethoxy-propane

Downstream raw materials:

methyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->6)-3,4-O-isopropylidene-α-D-galactopyranoside

C₂₂H₂₉NO₄

C₂₅H₃₂O₄Si

methyl 3,4-O-isopropylidene-6-O-(p-toluenesulfonyl)-α-D-galactopyranoside

Refernces

• 1、 Del Vigo, Enrique A.,Stortz, Carlos A.,Marino, Carla. "Regioselectivity of glycosylation reactions of galactose acceptors: An experimental and theoretical study". supporting information. p. 2982 - 2989. Retrieved 2020/01/09.
• 2、 Li, Cui-yun,Liu, Guang-jian,Du, Wei,Zhang, Yuan,Xing, Guo-wen. "A novel O-fucosylation strategy preactivated by (p-Tol)2SO/Tf2O and its application for the synthesis of Lewis blood group antigen Lewisa". supporting information. p. 2109 - 2112. Retrieved 2017/05/09.