Methyl 2-[5-acetyloxy-6-(methoxymethyl)-4-(2-methoxy-2-oxoethoxy)oxan-3-yl]oxyacetate

Base Information

• Chemical Name: Methyl 2-[5-acetyloxy-6-(methoxymethyl)-4-(2-methoxy-2-oxoethoxy)oxan-3-yl]oxyacetate
• CAS No.: 134121-16-7
• Molecular Formula: C₁₅H₂₄O₁₀
• Molecular Weight: 364.35
• DSSTox Substance ID: DTXSID30928460
• Mol file: 134121-16-7.mol

Synonyms:2,6-di-O-(methoxycarbonylmethyl)-3-O-methyl isomer of 4-O-acetyl-1,5-anhydro-di-O-(methoxycarbonylmethyl)-O-methylglucitol;3,6-di-O-(methoxycarbonylmethyl)-2-O-methyl isomer of 4-O-acetyl-1,5-anhydro-di-O-(methoxycarbonylmethyl)-O-methylglucitol;4-AACMG;4-O-acetyl-1,5-anhydro-di-O-(methoxycarbonylmethyl)-O-methylglucitol

Chemical Property of Methyl 2-[5-acetyloxy-6-(methoxymethyl)-4-(2-methoxy-2-oxoethoxy)oxan-3-yl]oxyacetate

Chemical Property:

• Vapor Pressure: 3.8E-08mmHg at 25°C
• Boiling Point: 445.9°Cat760mmHg
• Flash Point: 194.4°C
• PSA: 115.82000
• Density: 1.24g/cm³
• LogP: -0.92030
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 12
• Exact Mass: 364.13694696
• Heavy Atom Count: 25
• Complexity: 452

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1C(OCC(C1OCC(=O)OC)OCC(=O)OC)COC

Technology Process of Methyl 2-[5-acetyloxy-6-(methoxymethyl)-4-(2-methoxy-2-oxoethoxy)oxan-3-yl]oxyacetate

There total 5 articles about Methyl 2-[5-acetyloxy-6-(methoxymethyl)-4-(2-methoxy-2-oxoethoxy)oxan-3-yl]oxyacetate 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:

methyl 4,6-O-benzylidene-α-D-glucopyranoside (3162-96-7) → 4-O-acetyl-1,5-anhydro-2,3-di-O-(methoxycarbonylmethyl)-6-O-methyl-D-glucitol (134121-16-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / NaH / dimethylformamide / 2 h / 110 °C

2: 62 percent / LiAlH₄, AlCl₃ / diethyl ether; CH₂Cl₂ / 0.17 h / Heating

3: 90 percent / methylation

4: 65 percent / 50percent HOAc / 18 h / 70 °C

With lithium aluminium tetrahydride; aluminium trichloride; sodium hydride; acetic acid; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(91)84145-5

Reference yield:

(4aR,6S,7R,8S,8aR)-6-Methoxy-7,8-bis-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (134407-59-3) → 4-O-acetyl-1,5-anhydro-2,3-di-O-(methoxycarbonylmethyl)-6-O-methyl-D-glucitol (134121-16-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 62 percent / LiAlH₄, AlCl₃ / diethyl ether; CH₂Cl₂ / 0.17 h / Heating

2: 90 percent / methylation

3: 65 percent / 50percent HOAc / 18 h / 70 °C

With lithium aluminium tetrahydride; aluminium trichloride; acetic acid; In diethyl ether; dichloromethane;

DOI:10.1016/0008-6215(91)84145-5

Reference yield:

methyl 4-O-benzyl-2,3-di-O-p-methoxybenzyl-α-D-glucopyranoside (134407-60-6) → 4-O-acetyl-1,5-anhydro-2,3-di-O-(methoxycarbonylmethyl)-6-O-methyl-D-glucitol (134121-16-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / methylation

2: 65 percent / 50percent HOAc / 18 h / 70 °C

With acetic acid;

DOI:10.1016/0008-6215(91)84145-5

upstream raw materials:

(2S,3R,4R,5S,6R)-5-Benzyloxy-2-methoxy-6-methoxymethyl-tetrahydro-pyran-3,4-diol

bromoacetic acid methyl ester

methyl 4,6-O-benzylidene-α-D-glucopyranoside

methyl 4-O-benzyl-2,3-di-O-p-methoxybenzyl-α-D-glucopyranoside

Refernces