(2R,3R,4S,4aS,6S,7S,8aS)-4,7-Bis-benzyloxy-6-[(E)-3-((2R,3R,4S,4aS,8aS)-4-benzyloxy-3-methoxymethoxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propenyl]-3-methoxy-2-methoxymethyl-octahydro-pyrano[3,2-b]pyran

Base Information

• Chemical Name: (2R,3R,4S,4aS,6S,7S,8aS)-4,7-Bis-benzyloxy-6-[(E)-3-((2R,3R,4S,4aS,8aS)-4-benzyloxy-3-methoxymethoxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propenyl]-3-methoxy-2-methoxymethyl-octahydro-pyrano[3,2-b]pyran
• CAS No.: 172427-51-9
• Molecular Formula: C₄₅H₅₈O₁₁
• Molecular Weight: 774.949

Synonyms:(2R,3R,4S,4aS,6S,7S,8aS)-4,7-Bis-benzyloxy-6-[(E)-3-((2R,3R,4S,4aS,8aS)-4-benzyloxy-3-methoxymethoxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propenyl]-3-methoxy-2-methoxymethyl-octahydro-pyrano[3,2-b]pyran

Chemical Property of (2R,3R,4S,4aS,6S,7S,8aS)-4,7-Bis-benzyloxy-6-[(E)-3-((2R,3R,4S,4aS,8aS)-4-benzyloxy-3-methoxymethoxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propenyl]-3-methoxy-2-methoxymethyl-octahydro-pyrano[3,2-b]pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,4aS,6S,7S,8aS)-4,7-Bis-benzyloxy-6-[(E)-3-((2R,3R,4S,4aS,8aS)-4-benzyloxy-3-methoxymethoxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propenyl]-3-methoxy-2-methoxymethyl-octahydro-pyrano[3,2-b]pyran

There total 33 articles about (2R,3R,4S,4aS,6S,7S,8aS)-4,7-Bis-benzyloxy-6-[(E)-3-((2R,3R,4S,4aS,8aS)-4-benzyloxy-3-methoxymethoxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propenyl]-3-methoxy-2-methoxymethyl-octahydro-pyrano[3,2-b]pyran 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:

1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-2-propene (81972-19-2) → (2R,3R,4S,4aS,6S,7S,8aS)-4,7-Bis-benzyloxy-6-[(E)-3-((2R,3R,4S,4aS,8aS)-4-benzyloxy-3-methoxymethoxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propenyl]-3-methoxy-2-methoxymethyl-octahydro-pyrano[3,2-b]pyran (172427-51-9)

Guidance literature:

Multi-step reaction with 17 steps

1: 1.) 9-BBN, 2.) 30percent H₂O₂ / 1.) THF, RT; 2.) 3M NaOH, RT

2: Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

3: H₂ / Pd(OH)2/C / ethyl acetate; methanol / Ambient temperature

4: p-TsOH / CH₂Cl₂; dimethylformamide / Ambient temperature

5: 90 percent / KH / tetrahydrofuran / Ambient temperature

6: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / from -78 deg C to RT

7: L-Selectride / CH₂Cl₂ / -78 °C

8: 94 percent / NaH, TBAI / dimethylformamide

9: p-TsOH / CH₂Cl₂; methanol / Ambient temperature

10: i-Pr₂NEt / CH₂Cl₂ / Ambient temperature

11: NaH / dimethylformamide / Ambient temperature

12: PPTS / CH₂Cl₂; methanol

13: 94 percent / 2,6-di-t-butyl-4-methylpyridine / CH₂Cl₂ / -20 °C

14: 70 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

15: TBAF / tetrahydrofuran / Ambient temperature

16: Red-Al / diethyl ether / Ambient temperature

17: NaH, TBAI / dimethylformamide

With dmap; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; 2,6-di-tert-butyl-4-methylpyridine; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hydride; L-Selectride; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; palladium dihydroxide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(95)01973-L

Reference yield:

((2S,3S,4S,5R,6R)-3-Allyloxy-4-benzyloxy-5-methoxy-6-methoxymethyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester (172427-41-7) → (2R,3R,4S,4aS,6S,7S,8aS)-4,7-Bis-benzyloxy-6-[(E)-3-((2R,3R,4S,4aS,8aS)-4-benzyloxy-3-methoxymethoxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propenyl]-3-methoxy-2-methoxymethyl-octahydro-pyrano[3,2-b]pyran (172427-51-9)

Guidance literature:

Multi-step reaction with 19 steps

1: 1.) H₂; 2.) I₂ / 1.) 2MeP)2>PF₆ / 1.) THF; 2.) H₂O, RT

2: 2,6-lutidine / CH₂Cl₂ / Ambient temperature

3: DIBALH / CH₂Cl₂ / -78 °C

4: toluene / Ambient temperature

5: 92 percent / DIBALH / CH₂Cl₂ / -78 °C

6: t-BuOOH, (+)-DET, Ti(Oi-Pr)4, 4 Angstroem MS / CH₂Cl₂ / -20 °C

7: SO₃*Pyr, Et₃N, DMSO / CH₂Cl₂ / 0 °C

8: toluene / Ambient temperature

9: TBAF / tetrahydrofuran / Ambient temperature

10: Pd(PPh₃)4, Ph₃P / CH₂Cl₂ / Ambient temperature

11: 2,6-lutidine / CH₂Cl₂ / Ambient temperature

12: OsO₄, NMO / acetone; H₂O / Ambient temperature

13: NaIO₄ / tetrahydrofuran; H₂O / Ambient temperature

14: Ph₃P / CH₂Cl₂ / 0 °C

15: 73 percent / NaHMDS, n-BuLi / tetrahydrofuran / -78 °C

16: 70 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

17: TBAF / tetrahydrofuran / Ambient temperature

18: Red-Al / diethyl ether / Ambient temperature

19: NaH, TBAI / dimethylformamide

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; N-methyl-2-indolinone; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 Angstroem MS; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1016/0040-4039(95)01973-L

Reference yield:

3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1-propanol (173829-80-6) → (2R,3R,4S,4aS,6S,7S,8aS)-4,7-Bis-benzyloxy-6-[(E)-3-((2R,3R,4S,4aS,8aS)-4-benzyloxy-3-methoxymethoxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propenyl]-3-methoxy-2-methoxymethyl-octahydro-pyrano[3,2-b]pyran (172427-51-9)

Guidance literature:

Multi-step reaction with 16 steps

1: Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

2: H₂ / Pd(OH)2/C / ethyl acetate; methanol / Ambient temperature

3: p-TsOH / CH₂Cl₂; dimethylformamide / Ambient temperature

4: 90 percent / KH / tetrahydrofuran / Ambient temperature

5: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / from -78 deg C to RT

6: L-Selectride / CH₂Cl₂ / -78 °C

7: 94 percent / NaH, TBAI / dimethylformamide

8: p-TsOH / CH₂Cl₂; methanol / Ambient temperature

9: i-Pr₂NEt / CH₂Cl₂ / Ambient temperature

10: NaH / dimethylformamide / Ambient temperature

11: PPTS / CH₂Cl₂; methanol

12: 94 percent / 2,6-di-t-butyl-4-methylpyridine / CH₂Cl₂ / -20 °C

13: 70 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

14: TBAF / tetrahydrofuran / Ambient temperature

15: Red-Al / diethyl ether / Ambient temperature

16: NaH, TBAI / dimethylformamide

With dmap; n-butyllithium; 2,6-di-tert-butyl-4-methylpyridine; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hydride; L-Selectride; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; palladium dihydroxide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(95)01973-L

upstream raw materials:

benzyl bromide

1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-2-propene

(2R,4aR,8aS,9S,9aR,10aS)-9-Benzyloxy-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracene

((2S,3S,4S,5R,6R)-3-Allyloxy-4-benzyloxy-5-methoxy-6-methoxymethyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester

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