3,4,6-tri-O-acetyl-D-(U-¹³C)glucal

Base Information

• Chemical Name: 3,4,6-tri-O-acetyl-D-(U-¹³C)glucal
• CAS No.: 153362-93-7
• Molecular Formula: C₁₂H₁₆O₇
• Molecular Weight: 278.189
• Mol file: 153362-93-7.mol

Synonyms:

Chemical Property of 3,4,6-tri-O-acetyl-D-(U-¹³C)glucal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4,6-tri-O-acetyl-D-(U-¹³C)glucal

There total 1 articles about 3,4,6-tri-O-acetyl-D-(U-¹³C)glucal 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:

[glucose-U-(13)C6]-1,2,3,4,6-penta-O-acetyl-α/β-D-glucopyranose (299172-50-2) → 3,4,6-tri-O-acetyl-D-(U-13C)glucal (153362-93-7,478529-35-0,478529-37-2,478529-36-1)

Guidance literature:

[glucose-U-(13)C6]-1,2,3,4,6-penta-O-acetyl-α/β-D-glucopyranose; With hydrogen bromide; acetic acid; In dichloromethane; at 0 - 20 ℃; for 6h;

With copper(II) sulfate; acetic acid; zinc; sodium acetate; In water; ethyl acetate; at 0 - 20 ℃; for 2h;

DOI:10.1002/mrc.1364

Reference yield:

3,4,6-tri-O-acetyl-D-(U-13C)glucal (153362-93-7,478529-35-0,478529-37-2,478529-36-1) → p-cresyl 2,3,5-tri-O-acetyl-1-thio-α-D-[U-13C5]-arabinofuranoside (219627-30-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NaHCO₃, O₃, 2.) Me₂S, 3.) HOAc / 1.) MeOH, CH₂Cl₂, -78 deg C, 2.) -78 deg C to room temperature, 3.) MeOH, 70 deg C

2: H₂SO₄ / 0 °C

3: BF₃*Et₂O / CH₂Cl₂ / 0 °C

With dimethylsulfide; sulfuric acid; boron trifluoride diethyl etherate; sodium hydrogencarbonate; ozone; acetic acid; In dichloromethane;

DOI:10.1021/jo9815406

Reference yield:

3,4,6-tri-O-acetyl-D-(U-13C)glucal (153362-93-7,478529-35-0,478529-37-2,478529-36-1) → methyl 2,3,5-tri-O-acetyl-α-D-[U-13C5]-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-D-arabinofuranoside (219627-31-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaHCO₃, O₃, 2.) Me₂S, 3.) HOAc / 1.) MeOH, CH₂Cl₂, -78 deg C, 2.) -78 deg C to room temperature, 3.) MeOH, 70 deg C

2: H₂SO₄ / 0 °C

3: BF₃*Et₂O / CH₂Cl₂ / 0 °C

4: NIS, AgOTf / CH₂Cl₂ / 0 °C

With N-iodo-succinimide; dimethylsulfide; sulfuric acid; boron trifluoride diethyl etherate; silver trifluoromethanesulfonate; sodium hydrogencarbonate; ozone; acetic acid; In dichloromethane;

DOI:10.1021/jo9815406

upstream raw materials:

[glucose-U-(13)C6]-1,2,3,4,6-penta-O-acetyl-α/β-D-glucopyranose

Downstream raw materials:

3,4-di-O-benzyl-[13C₆]-D-arabino-hex-1-enitol

3,4-di-O-benzyl-6-O-levulinoyl-[13C₆]-D-arabino-hex-1-enitol

3,4-di-O-benzyl-6-O-triisopropylsilyl-[13C₆]-D-arabino-1-hex-1-enitol

dibutyl 3,4-di-O-benzyl-6-O-levulinoyl-2-O-pivaloyl-[13C₆]-D-glucopyranosyl phosphate