methyl 3-O-benzyl-6-O-(4-methoxybenzyl)-2-deoxy-α-D-threo-hexofuranos-5-uloside

Base Information

Chemical Name:methyl 3-O-benzyl-6-O-(4-methoxybenzyl)-2-deoxy-α-D-threo-hexofuranos-5-uloside
CAS No.:386765-77-1
Molecular Formula:C₂₂H₂₆O₆
Molecular Weight:386.445
Hs Code.:

Synonyms:methyl 3-O-benzyl-6-O-(4-methoxybenzyl)-2-deoxy-α-D-threo-hexofuranos-5-uloside

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Chemical Property of methyl 3-O-benzyl-6-O-(4-methoxybenzyl)-2-deoxy-α-D-threo-hexofuranos-5-uloside

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Technology Process of methyl 3-O-benzyl-6-O-(4-methoxybenzyl)-2-deoxy-α-D-threo-hexofuranos-5-uloside

There total 8 articles about methyl 3-O-benzyl-6-O-(4-methoxybenzyl)-2-deoxy-α-D-threo-hexofuranos-5-uloside 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: 100.0%

: 386765-75-9
methyl 3-O-benzyl-6-O-(4-methoxybenzyl)-2-deoxy-α-D-arabino-hexofuranoside

: 386765-77-1
methyl 3-O-benzyl-6-O-(4-methoxybenzyl)-2-deoxy-α-D-threo-hexofuranos-5-uloside

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 0 ℃; for 3.5h;
DOI:10.1246/bcsj.75.1927

Reference yield:

: 79241-07-9
(R)-4-((2S,3R)-3-(benzyloxy)-2,3-dihydrofuran-2-yl)-2,2-dimethyl-1,3-dioxolan

: 386765-77-1
methyl 3-O-benzyl-6-O-(4-methoxybenzyl)-2-deoxy-α-D-threo-hexofuranos-5-uloside

Guidance literature:: Multi-step reaction with 5 steps

1.1: Hg(OAc)2; water / tetrahydrofuran / 0.5 h / 25 °C

1.2: potassium iodide / tetrahydrofuran; H₂O / 0.25 h / 0 °C

1.3: NaBH₄ / tetrahydrofuran; H₂O / 1.5 h / 0 °C

2.1: 91 percent / acetic acid; water / 14 h / 25 °C

3.1: 69 percent / AcCl / 20 h / 0 °C

4.1: dibutyltin oxide / toluene / 2 h / Heating

4.2: 96 percent / CsF / dimethylformamide / 40 h / 80 °C

5.1: 100 percent / (COCl)2; dimethylsulfoxide; triethylamine / CH₂Cl₂ / 3.5 h / -78 - 0 °C

With oxalyl dichloride; mercury(II) diacetate; water; di(n-butyl)tin oxide; acetic acid; dimethyl sulfoxide; triethylamine; acetyl chloride; In tetrahydrofuran; dichloromethane; toluene; 5.1: Swern oxidation;
DOI:10.1246/bcsj.75.1927

Reference yield:

: (R)-1-((2R,3R)-3-Benzyloxy-5-hydroxy-tetrahydro-furan-2-yl)-ethane-1,2-diol

: 386765-77-1
methyl 3-O-benzyl-6-O-(4-methoxybenzyl)-2-deoxy-α-D-threo-hexofuranos-5-uloside

Guidance literature:: Multi-step reaction with 3 steps

1.1: AcCl / 0 °C

2.1: Bu₂SnO / toluene / Heating

2.2: 95 percent / CsF / dimethylformamide / 70 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

With oxalyl dichloride; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; acetyl chloride; In dichloromethane; toluene; 3.1: Swern oxidation;
DOI:10.1039/b104864n