methyl 2-O-acetyl-3-C-(2,5-anhydro-1-deoxy-3-O-acetyl-4,6,7-tri-O-benzyl-D-glycero-L-manno-heptit-1-yl)-4,6-O-benzylidene-3-deoxy-β-D-glucopyranoside

Base Information

Chemical Name:methyl 2-O-acetyl-3-C-(2,5-anhydro-1-deoxy-3-O-acetyl-4,6,7-tri-O-benzyl-D-glycero-L-manno-heptit-1-yl)-4,6-O-benzylidene-3-deoxy-β-D-glucopyranoside
CAS No.:263748-60-3
Molecular Formula:C₄₆H₅₂O₁₂
Molecular Weight:796.912
Hs Code.:

methyl 2-O-acetyl-3-C-(2,5-anhydro-1-deoxy-3-O-acetyl-4,6,7-tri-O-benzyl-D-glycero-L-manno-heptit-1-yl)-4,6-O-benzylidene-3-deoxy-β-D-glucopyranoside

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Chemical Property of methyl 2-O-acetyl-3-C-(2,5-anhydro-1-deoxy-3-O-acetyl-4,6,7-tri-O-benzyl-D-glycero-L-manno-heptit-1-yl)-4,6-O-benzylidene-3-deoxy-β-D-glucopyranoside

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Technology Process of methyl 2-O-acetyl-3-C-(2,5-anhydro-1-deoxy-3-O-acetyl-4,6,7-tri-O-benzyl-D-glycero-L-manno-heptit-1-yl)-4,6-O-benzylidene-3-deoxy-β-D-glucopyranoside

There total 10 articles about methyl 2-O-acetyl-3-C-(2,5-anhydro-1-deoxy-3-O-acetyl-4,6,7-tri-O-benzyl-D-glycero-L-manno-heptit-1-yl)-4,6-O-benzylidene-3-deoxy-β-D-glucopyranoside 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:

: 152006-40-1
3-O-allyl-4,6-O-benzylidene-2-O-p-methoxybenzyl-β-D-glucopyranoside

: 263748-60-3
methyl 2-O-acetyl-3-C-(2,5-anhydro-1-deoxy-3-O-acetyl-4,6,7-tri-O-benzyl-D-glycero-L-manno-heptit-1-yl)-4,6-O-benzylidene-3-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: 75 percent / NaH / dimethylformamide; methanol / 12 h / 0 °C

2.1: t-BuOK / dimethylsulfoxide / 1 h / 60 °C

2.2: 81 percent / HgO / acetone; H₂O

3.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 0.5 h / -78 - 20 °C

4.1: NaOH / tetrahydrofuran; pyridine / 2 h / -78 - 20 °C

5.1: 91 percent / DDQ / CH₂Cl₂; H₂O / 3.5 h / 0 - 20 °C

6.1: BuLi; Me₂SiCl₂; DMAP / tetrahydrofuran / -78 - 20 °C

6.2: Bu₃SnH; AIBN / toluene / 18 h / Heating

6.3: TBAF / tetrahydrofuran / 2 h / 20 °C

7.1: pyridine

With dmap; sodium hydroxide; n-butyllithium; oxalyl dichloride; potassium tert-butylate; sodium hydride; dimethyl sulfoxide; triethylamine; dimethylsilicon dichloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 1.1: Substitution / 2.1: Hydrolysis / 2.2: Hydrolysis / 3.1: Oxidation / 4.1: Condensation / 5.1: Hydrolysis / 6.1: Addition / 6.2: Reduction / 6.3: Hydrolysis / 7.1: Acetylation;
DOI:10.1080/07328300008544061

Reference yield:

: 263748-59-0
methyl 4,6-O-benzylidene-3-deoxy-3-C-methylene-β-D-ribo-hexopyranoside

: 263748-60-3
methyl 2-O-acetyl-3-C-(2,5-anhydro-1-deoxy-3-O-acetyl-4,6,7-tri-O-benzyl-D-glycero-L-manno-heptit-1-yl)-4,6-O-benzylidene-3-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: BuLi; Me₂SiCl₂; DMAP / tetrahydrofuran / -78 - 20 °C

1.2: Bu₃SnH; AIBN / toluene / 18 h / Heating

1.3: TBAF / tetrahydrofuran / 2 h / 20 °C

2.1: pyridine

With dmap; n-butyllithium; dimethylsilicon dichloride; In tetrahydrofuran; pyridine; 1.1: Addition / 1.2: Reduction / 1.3: Hydrolysis / 2.1: Acetylation;
DOI:10.1080/07328300008544061

Reference yield:

: (2R,4aR,6R,7S,8aR)-6-Methoxy-7-(4-methoxy-benzyloxy)-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one

: 263748-60-3
methyl 2-O-acetyl-3-C-(2,5-anhydro-1-deoxy-3-O-acetyl-4,6,7-tri-O-benzyl-D-glycero-L-manno-heptit-1-yl)-4,6-O-benzylidene-3-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaOH / tetrahydrofuran; pyridine / 2 h / -78 - 20 °C

2.1: 91 percent / DDQ / CH₂Cl₂; H₂O / 3.5 h / 0 - 20 °C

3.1: BuLi; Me₂SiCl₂; DMAP / tetrahydrofuran / -78 - 20 °C

3.2: Bu₃SnH; AIBN / toluene / 18 h / Heating

3.3: TBAF / tetrahydrofuran / 2 h / 20 °C

4.1: pyridine

With dmap; sodium hydroxide; n-butyllithium; dimethylsilicon dichloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; pyridine; dichloromethane; water; 1.1: Condensation / 2.1: Hydrolysis / 3.1: Addition / 3.2: Reduction / 3.3: Hydrolysis / 4.1: Acetylation;
DOI:10.1080/07328300008544061