1,2-O-cyclohexylidene-3,4,5-tri-O-benzyl-6-O-(2-azido-3,6-di-O-benzyl-2-deoxy-4-α-D-glucopyranosyl)-D-myo-inositol

Base Information

Chemical Name:1,2-O-cyclohexylidene-3,4,5-tri-O-benzyl-6-O-(2-azido-3,6-di-O-benzyl-2-deoxy-4-α-D-glucopyranosyl)-D-myo-inositol
CAS No.:491869-97-7
Molecular Formula:C₅₃H₅₉N₃O₁₀
Molecular Weight:898.066
Hs Code.:

Synonyms:1,2-O-cyclohexylidene-3,4,5-tri-O-benzyl-6-O-(2-azido-3,6-di-O-benzyl-2-deoxy-4-α-D-glucopyranosyl)-D-myo-inositol

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Chemical Property of 1,2-O-cyclohexylidene-3,4,5-tri-O-benzyl-6-O-(2-azido-3,6-di-O-benzyl-2-deoxy-4-α-D-glucopyranosyl)-D-myo-inositol

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Technology Process of 1,2-O-cyclohexylidene-3,4,5-tri-O-benzyl-6-O-(2-azido-3,6-di-O-benzyl-2-deoxy-4-α-D-glucopyranosyl)-D-myo-inositol

There total 9 articles about 1,2-O-cyclohexylidene-3,4,5-tri-O-benzyl-6-O-(2-azido-3,6-di-O-benzyl-2-deoxy-4-α-D-glucopyranosyl)-D-myo-inositol 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: 90.0%

: 491869-95-5
1,2-O-cyclohexylidene-3,4,5-tri-O-benzyl-6-O-(2-azido-3,6-di-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl)-D-myo-inositol

: 491869-97-7
1,2-O-cyclohexylidene-3,4,5-tri-O-benzyl-6-O-(2-azido-3,6-di-O-benzyl-2-deoxy-4-α-D-glucopyranosyl)-D-myo-inositol

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1016/S0040-4039(02)01590-3

Reference yield:

: 163039-18-7
(3aS,5R,6S,7S,7aS)-5-Hydroxymethyl-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

: 491869-97-7
1,2-O-cyclohexylidene-3,4,5-tri-O-benzyl-6-O-(2-azido-3,6-di-O-benzyl-2-deoxy-4-α-D-glucopyranosyl)-D-myo-inositol

Guidance literature:: Multi-step reaction with 7 steps

1.1: (Bu₃Sn)2O / benzene / Heating

1.2: Bu₄NI / benzene / 90 °C

2.1: NaH / dimethylformamide / 0.5 h / 0 °C

2.2: 6.4 g / TBAI / dimethylformamide

3.1: 98 percent / N-iodosuccinimide; Yb(OTf)3 / CH₂Cl₂

4.1: 87 percent / NaOMe; MeOH / CH₂Cl₂ / 24 h

5.1: 93 percent / pyridine; DMAP / CH₂Cl₂ / 8 h / -78 - 0 °C

6.1: 39 percent / TMSN₃; TBAF / tetrahydrofuran / 60 - 65 °C

7.1: 86 percent / BF₃*Et₂O / CH₂Cl₂ / 0.08 h / 0 °C

With pyridine; methanol; dmap; N-iodo-succinimide; trimethylsilylazide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; bis(tri-n-butyltin)oxide; ytterbium(III) triflate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja038807p

Reference yield:

: 491869-87-5
3,6-di-O-benzyl-4-O-p-methoxybenzyl-β-D-mannopyranose

: 491869-97-7
1,2-O-cyclohexylidene-3,4,5-tri-O-benzyl-6-O-(2-azido-3,6-di-O-benzyl-2-deoxy-4-α-D-glucopyranosyl)-D-myo-inositol

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / N-iodosuccinimide; Yb(OTf)3 / CH₂Cl₂

2: 87 percent / NaOMe; MeOH / CH₂Cl₂ / 24 h

3: 93 percent / pyridine; DMAP / CH₂Cl₂ / 8 h / -78 - 0 °C

4: 39 percent / TMSN₃; TBAF / tetrahydrofuran / 60 - 65 °C

5: 86 percent / BF₃*Et₂O / CH₂Cl₂ / 0.08 h / 0 °C

With pyridine; methanol; dmap; N-iodo-succinimide; trimethylsilylazide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; ytterbium(III) triflate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja038807p