Methyl 8-(hydroxymethyl)-4,4a,8,8a-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxine-4-carboxylate

Base Information

• Chemical Name: Methyl 8-(hydroxymethyl)-4,4a,8,8a-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxine-4-carboxylate
• CAS No.: 27934-92-5
• Molecular Formula: C9H14O7
• Molecular Weight: 234.2033
• NSC Number: 179466,170160
• DSSTox Substance ID: DTXSID20305307
• Mol file: 27934-92-5.mol

Synonyms:27934-92-5;methyl 8-(hydroxymethyl)-4,4a,8,8a-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxine-4-carboxylate;NSC170160;DTXSID20305307;NSC179466;NSC-170160;NSC-179466;Methyl 8-(hydroxymethyl)tetrahydro-2H,6H-[1,3]dioxino[5,4-d][1,3]dioxine-4-carboxylate (non-preferred name)

Chemical Property of Methyl 8-(hydroxymethyl)-4,4a,8,8a-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxine-4-carboxylate

Chemical Property:

• Vapor Pressure: 5.97E-06mmHg at 25°C
• Boiling Point: 339.8°Cat760mmHg
• Flash Point: 132.5°C
• Density: 1.309g/cm³
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 234.07395278
• Heavy Atom Count: 16
• Complexity: 256

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1C2C(C(OCO2)CO)OCO1

Technology Process of Methyl 8-(hydroxymethyl)-4,4a,8,8a-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxine-4-carboxylate

There total 4 articles about Methyl 8-(hydroxymethyl)-4,4a,8,8a-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxine-4-carboxylate 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: 90.0%

methanol (67-56-1) + 2,4:3,5-dimethylene-D-gluconic acid (5323-77-3) → methyl 2,4;3,5-di-O-methylene-D-gluconate (27934-92-5)

Guidance literature:

With toluene-4-sulfonic acid; for 12h; Heating;

DOI:10.1016/S0008-6215(02)00083-6

Reference yield:

2,4:3,5-dimethylene-D-gluconic acid (5323-77-3) → methyl 2,4;3,5-di-O-methylene-D-gluconate (27934-92-5)

Guidance literature:

With diazomethane; diethyl ether;

Reference yield:

D-Glucono-1,5-lactone (90-80-2,1335-57-5,4253-68-3) → methyl 2,4;3,5-di-O-methylene-D-gluconate (27934-92-5)

Guidance literature:

Multi-step reaction with 2 steps

1: cc HCl / 24 h / 20 °C

2: 90 percent / p-toluenesulfonic acid / 12 h / Heating

With hydrogenchloride; toluene-4-sulfonic acid;

DOI:10.1016/S0008-6215(02)00083-6

upstream raw materials:

2,4:3,5-dimethylene-D-gluconic acid

methanol

D-Glucono-1,5-lactone

Downstream raw materials:

methyl 2,4:3,5-Di-O-methylidene-6-O-tosyl-D-gluconate