1,5-di-O-(4-hydroxy-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-3-oxapentanediol

Base Information

Chemical Name:1,5-di-O-(4-hydroxy-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-3-oxapentanediol
CAS No.:172657-46-4
Molecular Formula:C₅₈H₆₆O₁₃
Molecular Weight:971.154
Hs Code.:

Synonyms:1,5-di-O-(4-hydroxy-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-3-oxapentanediol

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Chemical Property of 1,5-di-O-(4-hydroxy-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-3-oxapentanediol

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Technology Process of 1,5-di-O-(4-hydroxy-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-3-oxapentanediol

There total 4 articles about 1,5-di-O-(4-hydroxy-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-3-oxapentanediol 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:

: 172657-45-3
1,5-di-O-(4,6-O-benzylidene-2,3-di-O-benzyl-α-D-glukopyranosyl)-3-oxapentanediol

: 172657-46-4
1,5-di-O-(4-hydroxy-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-3-oxapentanediol

Guidance literature:: With hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; for 10h; Yield given; Ambient temperature;
DOI:10.1021/jo951870f

Reference yield:

: 103833-57-4
allyl 4,6-O-benzylidene-2,3-di-O-benzyl-α-D-glucopyranoside

: 172657-46-4
1,5-di-O-(4-hydroxy-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-3-oxapentanediol

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, MeOH, from -78 deg C to RT, 12 h

2: 92 percent / pyridine / CH₂Cl₂ / 22 h / Ambient temperature

3: 1.) NaH / 1.) THF, 70 deg C, 30 min, 2.) THF, reflux, 24 h

4: 67 percent / NaCNBH₃-HCl, 4A molecular sieves / tetrahydrofuran / 0.17 h / Ambient temperature

With pyridine; sodium tetrahydroborate; NaCNBH₃*HCl; 4 A molecular sieve; sodium hydride; ozone; In tetrahydrofuran; dichloromethane;
DOI:10.1080/00397919508011451

Reference yield:

: 172821-19-1
2-O-(4,6-O-benzylidene-2,3-di-O-benzyl-α-D-glucopyranosyl)ethanediol

: 172657-46-4
1,5-di-O-(4-hydroxy-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-3-oxapentanediol

Guidance literature:: Multi-step reaction with 3 steps

1: 92 percent / pyridine / CH₂Cl₂ / 22 h / Ambient temperature

2: 1.) NaH / 1.) THF, 70 deg C, 30 min, 2.) THF, reflux, 24 h

3: 67 percent / NaCNBH₃-HCl, 4A molecular sieves / tetrahydrofuran / 0.17 h / Ambient temperature

With pyridine; NaCNBH₃*HCl; 4 A molecular sieve; sodium hydride; In tetrahydrofuran; dichloromethane;
DOI:10.1080/00397919508011451