(2-O-benzoyl-3,4-di-O-benzyl-6-O-levulinoyl-α-D-mannopyranosyl)-(1->6)-1-O-allyl-3,4,5-tri-O-benzyl-2-O-naphthylmethyl-D-myo-inositol

Base Information

Chemical Name:(2-O-benzoyl-3,4-di-O-benzyl-6-O-levulinoyl-α-D-mannopyranosyl)-(1->6)-1-O-allyl-3,4,5-tri-O-benzyl-2-O-naphthylmethyl-D-myo-inositol
CAS No.:883878-67-9
Molecular Formula:C₇₃H₇₄O₁₄
Molecular Weight:1175.38
Hs Code.:

Synonyms:(2-O-benzoyl-3,4-di-O-benzyl-6-O-levulinoyl-α-D-mannopyranosyl)-(1->6)-1-O-allyl-3,4,5-tri-O-benzyl-2-O-naphthylmethyl-D-myo-inositol

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Chemical Property of (2-O-benzoyl-3,4-di-O-benzyl-6-O-levulinoyl-α-D-mannopyranosyl)-(1->6)-1-O-allyl-3,4,5-tri-O-benzyl-2-O-naphthylmethyl-D-myo-inositol

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Technology Process of (2-O-benzoyl-3,4-di-O-benzyl-6-O-levulinoyl-α-D-mannopyranosyl)-(1->6)-1-O-allyl-3,4,5-tri-O-benzyl-2-O-naphthylmethyl-D-myo-inositol

There total 11 articles about (2-O-benzoyl-3,4-di-O-benzyl-6-O-levulinoyl-α-D-mannopyranosyl)-(1->6)-1-O-allyl-3,4,5-tri-O-benzyl-2-O-naphthylmethyl-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: 93.0%

: 883878-66-8
(2-O-benzoyl-3,4-di-O-benzyl-α-D-mannopyranosyl)-(1->6)-1-O-allyl-3,4,5-tri-O-benzyl-2-O-naphthylmethyl-D-myo-inositol

: 123-76-2
levulinic acid

: 883878-67-9
(2-O-benzoyl-3,4-di-O-benzyl-6-O-levulinoyl-α-D-mannopyranosyl)-(1->6)-1-O-allyl-3,4,5-tri-O-benzyl-2-O-naphthylmethyl-D-myo-inositol

Guidance literature:: With dmap; diisopropyl-carbodiimide; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/ja0565368

Reference yield:

: (1S,2S,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-2,6-bis-(1-ethoxy-ethoxy)-cyclohexanol

: 883878-67-9
(2-O-benzoyl-3,4-di-O-benzyl-6-O-levulinoyl-α-D-mannopyranosyl)-(1->6)-1-O-allyl-3,4,5-tri-O-benzyl-2-O-naphthylmethyl-D-myo-inositol

Guidance literature:: Multi-step reaction with 6 steps

1.1: TBAI; NaH / dimethylformamide / 12 h / 0 - 20 °C

2.1: 5.6 g / aq. HCl / dimethylformamide; tetrahydrofuran / 2 h / 50 °C

3.1: TBAI; NaH / dimethylformamide / 0.5 h / 0 °C

3.2: 81 percent / dimethylformamide / -20 - 20 °C

4.1: TMSOTf / CH₂Cl₂ / 0.5 h / 0 °C

5.1: 1.20 g / AcCl; MeOH / CH₂Cl₂ / 7 h / 0 - 20 °C

6.1: 93 percent / diisopropylcarbodiimide; (dimethylamino)pyridine / CH₂Cl₂ / 2 h / 20 °C

With hydrogenchloride; methanol; dmap; trimethylsilyl trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; acetyl chloride; diisopropyl-carbodiimide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja0565368

Reference yield:

: Benzoic acid (3S,4S,5R,6R)-4,5-bis-benzyloxy-2-hydroxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl ester

: 883878-67-9
(2-O-benzoyl-3,4-di-O-benzyl-6-O-levulinoyl-α-D-mannopyranosyl)-(1->6)-1-O-allyl-3,4,5-tri-O-benzyl-2-O-naphthylmethyl-D-myo-inositol

Guidance literature:: Multi-step reaction with 4 steps

1: DBU / CH₂Cl₂ / 2 h / 0 °C

2: TMSOTf / CH₂Cl₂ / 0.5 h / 0 °C

3: 1.20 g / AcCl; MeOH / CH₂Cl₂ / 7 h / 0 - 20 °C

4: 93 percent / diisopropylcarbodiimide; (dimethylamino)pyridine / CH₂Cl₂ / 2 h / 20 °C

With methanol; dmap; trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; acetyl chloride; diisopropyl-carbodiimide; In dichloromethane;
DOI:10.1021/ja0565368