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

Base Information

Chemical Name:((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-methanol
CAS No.:181262-29-3
Molecular Formula:C₂₃H₂₈O₅
Molecular Weight:384.472
Hs Code.:

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

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

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

There total 13 articles about ((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-methanol 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:

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

: 181262-29-3
((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-methanol

Guidance literature:: Multi-step reaction with 13 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

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; 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

: 181262-29-3
((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-methanol

Guidance literature:: Multi-step reaction with 11 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

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; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1021/ja961230+

Reference yield:

: (2S,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-but-3-enyl-tetrahydro-pyran-2-ol

: 181262-29-3
((2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-methanol

Guidance literature:: Multi-step reaction with 12 steps

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

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

3: 98 percent / Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

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

5: 74 percent / NaH / dimethylformamide / 12 h / 23 °C

6: 77 percent / DMAP, Et₃N / CH₂Cl₂ / 72 h / 23 °C

7: 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

8: 96 percent / 1percent ethanolic HCl / 5 h / 23 °C

9: imidazole, pyridine / 11 h / 23 °C

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

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

12: 3percent methanolic HCl / 12 h / 23 °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; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol;
DOI:10.1021/ja961230+