1L-1,3-di-O-benzyl-2-azido-2-deoxy-4,5-O-methylidene-6-[(R)-(-)-O-(acetylmandeloyl)]-neo-inositol

Base Information

Chemical Name:1L-1,3-di-O-benzyl-2-azido-2-deoxy-4,5-O-methylidene-6-[(R)-(-)-O-(acetylmandeloyl)]-neo-inositol
CAS No.:1380085-14-2
Molecular Formula:C₃₁H₃₁N₃O₈
Molecular Weight:573.602
Hs Code.:

Synonyms:1L-1,3-di-O-benzyl-2-azido-2-deoxy-4,5-O-methylidene-6-[(R)-(-)-O-(acetylmandeloyl)]-neo-inositol

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Chemical Property of 1L-1,3-di-O-benzyl-2-azido-2-deoxy-4,5-O-methylidene-6-[(R)-(-)-O-(acetylmandeloyl)]-neo-inositol

Chemical Property:

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Technology Process of 1L-1,3-di-O-benzyl-2-azido-2-deoxy-4,5-O-methylidene-6-[(R)-(-)-O-(acetylmandeloyl)]-neo-inositol

There total 8 articles about 1L-1,3-di-O-benzyl-2-azido-2-deoxy-4,5-O-methylidene-6-[(R)-(-)-O-(acetylmandeloyl)]-neo-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: 48.0%

: rac-1,3-di-O-benzyl-2-azido-2-deoxy-4,5-O-methylidene-neo-inositol

: 51019-43-3
(R)-(-)-O-acetylmandelic acid

: 1380085-14-2
1L-1,3-di-O-benzyl-2-azido-2-deoxy-4,5-O-methylidene-6-[(R)-(-)-O-(acetylmandeloyl)]-neo-inositol

: 1380085-16-4
1D-1,3-di-O-benzyl-2-azido-2-deoxy-4,5-O-methylidene-6-[(R)-(-)-O-(acetylmandeloyl)]-neo-inositol

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1021/jo300444b

Reference yield:

: 100-39-0
benzyl bromide

: 1380085-14-2
1L-1,3-di-O-benzyl-2-azido-2-deoxy-4,5-O-methylidene-6-[(R)-(-)-O-(acetylmandeloyl)]-neo-inositol

Guidance literature:: Multi-step reaction with 8 steps

1.1: lithium hydride / N,N-dimethyl-formamide / 1 h / 20 °C

1.2: 12 h / 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 20 °C

2.2: 3 h / 20 °C

3.1: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / 0 - 20 °C

4.1: pyridine / dichloromethane / 1.25 h / -10 - 20 °C

5.1: sodium azide / N,N,N,N,N,N-hexamethylphosphoric triamide / 12 h / 20 °C

6.1: hydrogenchloride / tetrahydrofuran; methanol; water / 2 h / Reflux

7.1: trichlorophosphate / dimethyl sulfoxide / 3 h / 65 °C

8.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 12 h / 20 °C

With pyridine; hydrogenchloride; dmap; sodium azide; lithium hydride; sodium hydride; diisobutylaluminium hydride; dicyclohexyl-carbodiimide; trichlorophosphate; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo300444b

Reference yield:

: 1380085-00-6
C₃₀H₃₁F₃O₉S

: 1380085-14-2
1L-1,3-di-O-benzyl-2-azido-2-deoxy-4,5-O-methylidene-6-[(R)-(-)-O-(acetylmandeloyl)]-neo-inositol

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium azide / N,N-dimethyl-formamide / 1 h / 100 °C / Inert atmosphere

2.1: hydrogenchloride / tetrahydrofuran; methanol; water / 2 h / Reflux

3.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / 1 h / 0 - 20 °C

3.2: 12 h / Reflux

4.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 12 h / 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; dmap; sodium azide; trimethylsilyl trifluoromethanesulfonate; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo300444b