((2R,3R,4S,5S,6S)-4-Benzyloxy-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-yl)-acetonitrile

Base Information

Chemical Name:((2R,3R,4S,5S,6S)-4-Benzyloxy-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-yl)-acetonitrile
CAS No.:157219-90-4
Molecular Formula:C₁₆H₂₁NO₄
Molecular Weight:291.347
Hs Code.:

Synonyms:((2R,3R,4S,5S,6S)-4-Benzyloxy-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-yl)-acetonitrile

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Chemical Property of ((2R,3R,4S,5S,6S)-4-Benzyloxy-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-yl)-acetonitrile

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Technology Process of ((2R,3R,4S,5S,6S)-4-Benzyloxy-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-yl)-acetonitrile

There total 8 articles about ((2R,3R,4S,5S,6S)-4-Benzyloxy-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-yl)-acetonitrile 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: 70.0%

: 143-33-9,25596-52-5
sodium cyanide

: 157219-89-1
Toluene-4-sulfonic acid (2R,3S,4S,5S,6S)-4-benzyloxy-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester

: 157219-90-4
((2R,3R,4S,5S,6S)-4-Benzyloxy-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-yl)-acetonitrile

Guidance literature:: In dimethyl sulfoxide; at 70 ℃; for 1.5h;
DOI:10.1021/jo990988j

Reference yield:

: 109958-35-2
(2R,4aR,6S,7S,8S,8aS)-8-Benzyloxy-6-methoxy-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

: 157219-90-4
((2R,3R,4S,5S,6S)-4-Benzyloxy-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-yl)-acetonitrile

Guidance literature:: Multi-step reaction with 3 steps

1: 98 percent / p-toluenesulfonic acid monohydrate / methanol / 1.5 h / 20 °C

2: 47.10 g / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 4 h / 0 °C

3: 70 percent / dimethylsulfoxide / 1.5 h / 70 °C

With dmap; toluene-4-sulfonic acid; triethylamine; In methanol; dichloromethane; dimethyl sulfoxide; 1: Hydrolysis / 2: Tosylation / 3: Substitution;
DOI:10.1021/jo990988j

Reference yield:

: 68907-47-1
methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-altro-pyranoside

: 157219-90-4
((2R,3R,4S,5S,6S)-4-Benzyloxy-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-yl)-acetonitrile

Guidance literature:: Multi-step reaction with 4 steps

1: 99 percent / tetra-n-butylammonium iodide; sodium hydride / tetrahydrofuran; dimethylformamide; various solvent(s) / 20 °C

2: 98 percent / p-toluenesulfonic acid monohydrate / methanol / 1.5 h / 20 °C

3: 47.10 g / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 4 h / 0 °C

4: 70 percent / dimethylsulfoxide / 1.5 h / 70 °C

With dmap; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 1: Alkylation / 2: Hydrolysis / 3: Tosylation / 4: Substitution;
DOI:10.1021/jo990988j