(2S,3R,4R,5R,6R,2'R,3'R,4'R,5'R)-6'-<3,4-Bis(benzyloxy)-5-ethyl-tetrahydro-2-methoxy-2H-pyran-6-yl>-3'-methoxy-5'-<(methoxymethyl)oxy>-2',4'-dimethyl-1'-hexanal

Base Information

Chemical Name:(2S,3R,4R,5R,6R,2'R,3'R,4'R,5'R)-6'-<3,4-Bis(benzyloxy)-5-ethyl-tetrahydro-2-methoxy-2H-pyran-6-yl>-3'-methoxy-5'-<(methoxymethyl)oxy>-2',4'-dimethyl-1'-hexanal
CAS No.:172603-20-2
Molecular Formula:C₃₃H₄₈O₈
Molecular Weight:572.739
Hs Code.:

Synonyms:(2S,3R,4R,5R,6R,2'R,3'R,4'R,5'R)-6'-<3,4-Bis(benzyloxy)-5-ethyl-tetrahydro-2-methoxy-2H-pyran-6-yl>-3'-methoxy-5'-<(methoxymethyl)oxy>-2',4'-dimethyl-1'-hexanal

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Chemical Property of (2S,3R,4R,5R,6R,2'R,3'R,4'R,5'R)-6'-<3,4-Bis(benzyloxy)-5-ethyl-tetrahydro-2-methoxy-2H-pyran-6-yl>-3'-methoxy-5'-<(methoxymethyl)oxy>-2',4'-dimethyl-1'-hexanal

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Technology Process of (2S,3R,4R,5R,6R,2'R,3'R,4'R,5'R)-6'-<3,4-Bis(benzyloxy)-5-ethyl-tetrahydro-2-methoxy-2H-pyran-6-yl>-3'-methoxy-5'-<(methoxymethyl)oxy>-2',4'-dimethyl-1'-hexanal

There total 18 articles about (2S,3R,4R,5R,6R,2'R,3'R,4'R,5'R)-6'-<3,4-Bis(benzyloxy)-5-ethyl-tetrahydro-2-methoxy-2H-pyran-6-yl>-3'-methoxy-5'-<(methoxymethyl)oxy>-2',4'-dimethyl-1'-hexanal 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:

: 172603-19-9
(2S,3R,4R,5R,6R,2'S,3'R,4'R,5'R)-6'-<3,4-Bis(benzyloxy)-5-ethyl-tetrahydro-2-methoxy-2H-pyran-6-yl>-3'-methoxy-5'-<(methoxymethyl)oxy>-2',4'-dimethyl-1'-hexanol

: 172603-20-2
(2S,3R,4R,5R,6R,2'R,3'R,4'R,5'R)-6'-<3,4-Bis(benzyloxy)-5-ethyl-tetrahydro-2-methoxy-2H-pyran-6-yl>-3'-methoxy-5'-<(methoxymethyl)oxy>-2',4'-dimethyl-1'-hexanal

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.5h; Yield given;
DOI:10.1021/jo00128a032

Reference yield:

: 108393-28-8
(2S,3R,4S)-5-benzyloxy-2,3-dimethylpentane-1,4-diol

: 172603-20-2
(2S,3R,4R,5R,6R,2'R,3'R,4'R,5'R)-6'-<3,4-Bis(benzyloxy)-5-ethyl-tetrahydro-2-methoxy-2H-pyran-6-yl>-3'-methoxy-5'-<(methoxymethyl)oxy>-2',4'-dimethyl-1'-hexanal

Guidance literature:: Multi-step reaction with 11 steps

1: imidazole / dimethylformamide / 14 h / 25 °C

2: NaH / dimethylformamide / 1.) 0 deg C, 30 min, 2.) 25 deg C, 1 h

3: 86 percent / H₂ / PdCl₂ / methanol / 0.33 h

4: 99 percent / Et₃N, DMAP / CH₂Cl₂ / 2.5 h / 25 °C

5: 95 percent / NaI / acetone / 15 h / Heating

6: 97 percent / acetonitrile / 45 h / Heating

7: n-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C to -40 deg C, 2.) 20 deg C, 3 h

8: 1.) B₂H₆*THF, 2.) 3 N NaOH, 30percent H₂O₂ / 1.) THF, 15-20 deg C, 30 min, 2.) EtOH, 40 deg C, 30 min

9: 100 percent / i-Pr₂NEt / CH₂Cl₂ / 1.) 25 deg C, 5 h, 2.) 40 deg C, 2.5 h

10: 99 percent / nBu₄NF / tetrahydrofuran / 2.5 h / 25 °C

11: DMSO, (COCl)2 / CH₂Cl₂ / 0.5 h / -78 °C

With 1H-imidazole; dmap; sodium hydroxide; n-butyllithium; oxalyl dichloride; B₂H₆-THF; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; palladium dichloride; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1021/jo00128a032

Reference yield:

: 172603-11-1
(2R,3S,4R)-1-(Benzyloxy)-5-<(tert-butyldiphenylsilyl)oxy>-3-methoxy-2,4-dimethylpentane

: 172603-20-2
(2S,3R,4R,5R,6R,2'R,3'R,4'R,5'R)-6'-<3,4-Bis(benzyloxy)-5-ethyl-tetrahydro-2-methoxy-2H-pyran-6-yl>-3'-methoxy-5'-<(methoxymethyl)oxy>-2',4'-dimethyl-1'-hexanal

Guidance literature:: Multi-step reaction with 9 steps

1: 86 percent / H₂ / PdCl₂ / methanol / 0.33 h

2: 99 percent / Et₃N, DMAP / CH₂Cl₂ / 2.5 h / 25 °C

3: 95 percent / NaI / acetone / 15 h / Heating

4: 97 percent / acetonitrile / 45 h / Heating

5: n-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C to -40 deg C, 2.) 20 deg C, 3 h

6: 1.) B₂H₆*THF, 2.) 3 N NaOH, 30percent H₂O₂ / 1.) THF, 15-20 deg C, 30 min, 2.) EtOH, 40 deg C, 30 min

7: 100 percent / i-Pr₂NEt / CH₂Cl₂ / 1.) 25 deg C, 5 h, 2.) 40 deg C, 2.5 h

8: 99 percent / nBu₄NF / tetrahydrofuran / 2.5 h / 25 °C

9: DMSO, (COCl)2 / CH₂Cl₂ / 0.5 h / -78 °C

With dmap; sodium hydroxide; n-butyllithium; oxalyl dichloride; B₂H₆-THF; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; palladium dichloride; In tetrahydrofuran; methanol; hexane; dichloromethane; acetone; acetonitrile;
DOI:10.1021/jo00128a032