((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-acetonitrile

Base Information

Chemical Name:((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-acetonitrile
CAS No.:181265-63-4
Molecular Formula:C₂₄H₂₇NO₄
Molecular Weight:393.483
Hs Code.:

Synonyms:((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-acetonitrile

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Chemical Property of ((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-acetonitrile

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Technology Process of ((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-acetonitrile

There total 15 articles about ((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-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: 98.0%

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

: 181265-57-6
Methanesulfonic acid (2R,3R,4S,4aS,8aS)-3,4-bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

: 181265-63-4
((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-acetonitrile

Guidance literature:: In dimethyl sulfoxide; at 90 ℃; for 1.5h;
DOI:10.1021/ja961230+

Reference yield:

: 82598-84-3
2,3,4,6-tetra-O-benzyl-D-galactonolactone

: 181265-63-4
((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-acetonitrile

Guidance literature:: Multi-step reaction with 15 steps

1: diethyl ether / 0.25 h / -78 °C

2: Et₃SiH, BF₃*Et₂O / CH₂Cl₂; acetonitrile / 0.25 h / -20 °C

3: 1.) O₃, 2.) NaBH₄ / 1.) MeOH, CH₂Cl₂

4: 98 percent / Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

5: 100 percent / H₂ / Pd(OH)2/C / methanol / 4 h / 23 °C

6: 74 percent / NaH / dimethylformamide / 12 h / 23 °C

7: 77 percent / DMAP, Et₃N / CH₂Cl₂ / 72 h / 23 °C

8: 1.) 1,1'-thiocarbonyldiimidazole, 2.) 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine / 1.) toluene, 110 deg C, 4 h, 2.) 23 deg C, 3 h

9: 96 percent / 1percent ethanolic HCl / 5 h / 23 °C

10: imidazole, pyridine / 11 h / 23 °C

11: OsO₄, NMO / 2-methyl-propan-2-ol; acetone; H₂O / 48 h / 23 °C

12: 1.) Ag₂O, 2.) n-Bu₄NI, NaH / 1.) Et₂O, 35 deg C, 12 h, 2.) THF, 23 deg C, 5 h

13: 3percent methanolic HCl / 12 h / 23 °C

14: 96 percent / Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

15: 98 percent / dimethylsulfoxide / 1.5 h / 90 °C

With pyridine; 1H-imidazole; 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine; hydrogenchloride; triethylsilane; dmap; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; boron trifluoride diethyl etherate; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; triethylamine; 1,1'-Thiocarbonyldiimidazole; silver(l) oxide; palladium dihydroxide; In methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol;
DOI:10.1021/ja961230+

Reference yield:

: 181262-24-8
1-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)-3-butene

: 181265-63-4
((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-acetonitrile

Guidance literature:: Multi-step reaction with 13 steps

1: 1.) O₃, 2.) NaBH₄ / 1.) MeOH, CH₂Cl₂

2: 98 percent / Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

3: 100 percent / H₂ / Pd(OH)2/C / methanol / 4 h / 23 °C

4: 74 percent / NaH / dimethylformamide / 12 h / 23 °C

5: 77 percent / DMAP, Et₃N / CH₂Cl₂ / 72 h / 23 °C

6: 1.) 1,1'-thiocarbonyldiimidazole, 2.) 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine / 1.) toluene, 110 deg C, 4 h, 2.) 23 deg C, 3 h

7: 96 percent / 1percent ethanolic HCl / 5 h / 23 °C

8: imidazole, pyridine / 11 h / 23 °C

9: OsO₄, NMO / 2-methyl-propan-2-ol; acetone; H₂O / 48 h / 23 °C

10: 1.) Ag₂O, 2.) n-Bu₄NI, NaH / 1.) Et₂O, 35 deg C, 12 h, 2.) THF, 23 deg C, 5 h

11: 3percent methanolic HCl / 12 h / 23 °C

12: 96 percent / Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

13: 98 percent / dimethylsulfoxide / 1.5 h / 90 °C

With pyridine; 1H-imidazole; 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine; hydrogenchloride; dmap; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; triethylamine; 1,1'-Thiocarbonyldiimidazole; silver(l) oxide; palladium dihydroxide; In methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1021/ja961230+