2L-2,4/3-3,4-diacetyloxy-2-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyloxy)-cyclohex-5-enone

Base Information

• Chemical Name: 2L-2,4/3-3,4-diacetyloxy-2-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyloxy)-cyclohex-5-enone
• CAS No.: 77987-41-8
• Molecular Formula: C₂₄H₃₀O₁₅
• Molecular Weight: 558.493
• Mol file: 77987-41-8.mol

Synonyms:2L-2,4/3-3,4-diacetyloxy-2-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyloxy)-cyclohex-5-enone

Chemical Property of 2L-2,4/3-3,4-diacetyloxy-2-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyloxy)-cyclohex-5-enone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2L-2,4/3-3,4-diacetyloxy-2-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyloxy)-cyclohex-5-enone

There total 7 articles about 2L-2,4/3-3,4-diacetyloxy-2-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyloxy)-cyclohex-5-enone 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 6-deoxy-2,2',3,3',4',6'-hexa-O-acetyl-6-iodo-β-maltoside (25787-32-0) → 2L-2,4/3-3,4-diacetyloxy-2-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyloxy)-cyclohex-5-enone (77987-41-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / DBU / toluene / 4 h / 60 - 70 °C

2: 1.) aq. HgCl₂, 2.) pyridine, Ac₂O / 1.) acetone, reflux, 4 h, 2.) r.t., overnight

With pyridine; acetic anhydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; mercury dichloride; In toluene;

Reference yield:

2,3-di-O-acetyl-1,6-anhydro-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glycopyranose (28868-67-9) → 2L-2,4/3-3,4-diacetyloxy-2-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyloxy)-cyclohex-5-enone (77987-41-8)

Guidance literature:

Multi-step reaction with 5 steps

1: hydrogenchloride; zinc(II) iodide / 1.) 1,2-dichloroethane, RT, 4,5 h 2.) methanol, 0 deg C, 10 min

2: pyridine / Ambient temperature

3: lithium iodide / diethyl ether / 24 h / Ambient temperature

4: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 5 h / 75 - 80 °C

5: pyridine; acetic anhydride; mercury dichloride / 1.) acetone-water, RT, 2 d 2.) 0 deg C, 1 d

With pyridine; hydrogenchloride; acetic anhydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; mercury dichloride; zinc(II) iodide; lithium iodide; In diethyl ether; toluene;

Reference yield:

Acetic acid (2S,3R,4S,5S,6S)-3-acetoxy-6-iodomethyl-2-phenylsulfanyl-5-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester (130130-54-0) → 2L-2,4/3-3,4-diacetyloxy-2-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyloxy)-cyclohex-5-enone (77987-41-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 5 h / 75 - 80 °C

2: pyridine; acetic anhydride; mercury dichloride / 1.) acetone-water, RT, 2 d 2.) 0 deg C, 1 d

With pyridine; acetic anhydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; mercury dichloride; In toluene;

upstream raw materials:

phenyl 2,3-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-6-deoxy-1-thio-β-D-xylo-hexo-5-enopyranoside

methyl 2,3-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-6-deoxy-β-D-xylo-hex-5-enopyranoside

methyl 6-deoxy-2,2',3,3',4',6'-hexa-O-acetyl-6-iodo-β-maltoside

2,3-di-O-acetyl-1,6-anhydro-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glycopyranose