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

Base Information

Chemical Name:((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-acetaldehyde
CAS No.:181265-71-4
Molecular Formula:C₂₄H₂₈O₅
Molecular Weight:396.483
Hs Code.:

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

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

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

There total 16 articles about ((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-acetaldehyde 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: 94.0%

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

: 181265-71-4
((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-acetaldehyde

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -78 ℃; for 0.166667h;
DOI:10.1021/ja961230+

Reference yield:

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

: 181265-71-4
((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-acetaldehyde

Guidance literature:: Multi-step reaction with 16 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

16: 94 percent / DIBAL / toluene / 0.17 h / -78 °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; diisobutylaluminium hydride; ozone; triethylamine; 1,1'-Thiocarbonyldiimidazole; silver(l) oxide; palladium dihydroxide; In methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; 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

: 181265-71-4
((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-acetaldehyde

Guidance literature:: Multi-step reaction with 14 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

14: 94 percent / DIBAL / toluene / 0.17 h / -78 °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; diisobutylaluminium hydride; ozone; triethylamine; 1,1'-Thiocarbonyldiimidazole; silver(l) oxide; palladium dihydroxide; In methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;
DOI:10.1021/ja961230+