((2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-vinyl-octahydro-pyrano[3,2-b]pyran-2-yl)-acetonitrile

Base Information

Chemical Name:((2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-vinyl-octahydro-pyrano[3,2-b]pyran-2-yl)-acetonitrile
CAS No.:172427-36-0
Molecular Formula:C₃₃H₃₅NO₅
Molecular Weight:525.645
Hs Code.:

Synonyms:((2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-vinyl-octahydro-pyrano[3,2-b]pyran-2-yl)-acetonitrile

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Chemical Property of ((2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-vinyl-octahydro-pyrano[3,2-b]pyran-2-yl)-acetonitrile

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Technology Process of ((2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-vinyl-octahydro-pyrano[3,2-b]pyran-2-yl)-acetonitrile

There total 5 articles about ((2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-vinyl-octahydro-pyrano[3,2-b]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: 92.0%

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

: 172427-35-9
Toluene-4-sulfonic acid (2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-tris-benzyloxy-6-vinyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

: 172427-36-0
((2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-vinyl-octahydro-pyrano[3,2-b]pyran-2-yl)-acetonitrile

Guidance literature:: In dimethyl sulfoxide; at 70 ℃;
DOI:10.1016/0040-4039(95)01972-K

Reference yield:

: 100-39-0
benzyl bromide

: 172427-36-0
((2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-vinyl-octahydro-pyrano[3,2-b]pyran-2-yl)-acetonitrile

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / NaH / tetrahydrofuran; dimethylformamide / Ambient temperature

2: 89 percent / CAN / acetonitrile; H₂O / Ambient temperature

3: 92 percent / Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

4: 92 percent / dimethylsulfoxide / 70 °C

With dmap; ammonium cerium(IV) nitrate; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/0040-4039(95)01972-K

Reference yield:

: 172427-34-8
((2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-vinyl-octahydro-pyrano[3,2-b]pyran-2-yl)-methanol

: 172427-36-0
((2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-vinyl-octahydro-pyrano[3,2-b]pyran-2-yl)-acetonitrile

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

2: 92 percent / dimethylsulfoxide / 70 °C

With dmap; triethylamine; In dichloromethane; dimethyl sulfoxide;
DOI:10.1016/0040-4039(95)01972-K