[(2R,3S,4S,5R,6R)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetonitrile

Base Information

Chemical Name:[(2R,3S,4S,5R,6R)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetonitrile
CAS No.:797035-75-7
Molecular Formula:C₂₂H₃₁NO₅
Molecular Weight:389.492
Hs Code.:

Synonyms:[(2R,3S,4S,5R,6R)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetonitrile

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Chemical Property of [(2R,3S,4S,5R,6R)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetonitrile

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Technology Process of [(2R,3S,4S,5R,6R)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetonitrile

There total 2 articles about [(2R,3S,4S,5R,6R)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-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: 81.0%

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

: 797035-74-6
(2R,3R,4R,5R,6S)-2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-iodomethyl-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran

: 797035-75-7
[(2R,3S,4S,5R,6R)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetonitrile

Guidance literature:: In dimethyl sulfoxide; at 75 ℃; for 12h;
DOI:10.1002/chem.200500892

Reference yield:

: 797035-72-4
(2R,3R,4R,5R,6S)-2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-iodomethyl-3,5-dimethyl-tetrahydro-pyran-4-ol

: 797035-75-7
[(2R,3S,4S,5R,6R)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetonitrile

Guidance literature:: Multi-step reaction with 2 steps

1: 79.3 percent / BF₃*Et₂O / CH₂Cl₂ / 0.5 h / 0 °C

2: 81 percent / dimethylsulfoxide / 12 h / 75 °C

With boron trifluoride diethyl etherate; In dichloromethane; dimethyl sulfoxide;
DOI:10.1002/chem.200500892

Reference yield: 72.0%

: 797035-75-7
[(2R,3S,4S,5R,6R)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetonitrile

: 797035-76-8
2-[(2R,3S,4S,5R,6R)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanol

Guidance literature:: [(2R,3S,4S,5R,6R)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetonitrile; With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 1h;

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.5h;
DOI:10.1021/ol048275x