(2S,3S,4R,5S)-2-[(S)-3-(3-Benzyloxymethoxy-phenyl)-3-methoxy-propyl]-6-(tert-butyl-dimethyl-silanyloxy)-4-methyl-5-(tetrahydro-pyran-2-yloxy)-hexane-1,3-diol

Base Information

Chemical Name:(2S,3S,4R,5S)-2-[(S)-3-(3-Benzyloxymethoxy-phenyl)-3-methoxy-propyl]-6-(tert-butyl-dimethyl-silanyloxy)-4-methyl-5-(tetrahydro-pyran-2-yloxy)-hexane-1,3-diol
CAS No.:137531-87-4
Molecular Formula:C₃₆H₅₈O₈Si
Molecular Weight:646.937
Hs Code.:

(2S,3S,4R,5S)-2-[(S)-3-(3-Benzyloxymethoxy-phenyl)-3-methoxy-propyl]-6-(tert-butyl-dimethyl-silanyloxy)-4-methyl-5-(tetrahydro-pyran-2-yloxy)-hexane-1,3-diol

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Chemical Property of (2S,3S,4R,5S)-2-[(S)-3-(3-Benzyloxymethoxy-phenyl)-3-methoxy-propyl]-6-(tert-butyl-dimethyl-silanyloxy)-4-methyl-5-(tetrahydro-pyran-2-yloxy)-hexane-1,3-diol

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Technology Process of (2S,3S,4R,5S)-2-[(S)-3-(3-Benzyloxymethoxy-phenyl)-3-methoxy-propyl]-6-(tert-butyl-dimethyl-silanyloxy)-4-methyl-5-(tetrahydro-pyran-2-yloxy)-hexane-1,3-diol

There total 23 articles about (2S,3S,4R,5S)-2-[(S)-3-(3-Benzyloxymethoxy-phenyl)-3-methoxy-propyl]-6-(tert-butyl-dimethyl-silanyloxy)-4-methyl-5-(tetrahydro-pyran-2-yloxy)-hexane-1,3-diol 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:

: 110-87-2
3,4-dihydro-2H-pyran

: 137531-87-4
(2S,3R,4R,5R,8S)-8-(m-benzyloxymethoxyphenyl)-1-(tert-butyldimethylsiloxy)-5-hydroxymethyl-8-methoxy-3-methyl-2-(2-tetrahydropyranyloxy)octan-4-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 6 h / Ambient temperature

2: 85 percent / lithium aluminum hydride / tetrahydrofuran / 1 h / -78 °C

3: 95 percent / triethylamine, 4-DMAP / CH₂Cl₂ / 12 h / Ambient temperature

4: 88 percent / H₂ / Pd/C / ethanol / 8 h

5: CuI / tetrahydrofuran

With dmap; lithium aluminium tetrahydride; hydrogen; pyridinium p-toluenesulfonate; triethylamine; palladium on activated charcoal; copper(l) iodide; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1016/S0040-4020(01)81547-7

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 137531-87-4
(2S,3R,4R,5R,8S)-8-(m-benzyloxymethoxyphenyl)-1-(tert-butyldimethylsiloxy)-5-hydroxymethyl-8-methoxy-3-methyl-2-(2-tetrahydropyranyloxy)octan-4-ol

Guidance literature:: Multi-step reaction with 9 steps

2: 92 percent / diisobutyl aluminum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

3: 90 percent / (-)-diisopropyl tartrate, titanium tetraisopropoxide, t-butyl hydroperoxide, MS 4 Angstroem / CH₂Cl₂; toluene / 11 h / -20 °C

4: 91 percent / Red-al / toluene; tetrahydrofuran / 10.2 h / 0 °C

5: 93 percent / triethylamine, 4-DMAP / CH₂Cl₂ / 4 h / Ambient temperature

6: sodium hydride / tetrahydrofuran; dimethylformamide / 5 h / Ambient temperature

7: sodium bromide / dimethylformamide / 48 h / Ambient temperature

8: Mg / tetrahydrofuran / 1 h / Irradiation

9: CuI / tetrahydrofuran

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; (-)-diisopropyl tartrate; MS 4 Angstroem; sodium hydride; diisobutylaluminium hydride; magnesium; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium bromide; copper(l) iodide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4020(01)81547-7

Reference yield:

: 14755-02-3,588-30-7
3-hydroxy-trans-cinnamic acid

: 137531-87-4
(2S,3R,4R,5R,8S)-8-(m-benzyloxymethoxyphenyl)-1-(tert-butyldimethylsiloxy)-5-hydroxymethyl-8-methoxy-3-methyl-2-(2-tetrahydropyranyloxy)octan-4-ol

Guidance literature:: Multi-step reaction with 9 steps

2: 92 percent / diisobutyl aluminum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

3: 90 percent / (-)-diisopropyl tartrate, titanium tetraisopropoxide, t-butyl hydroperoxide, MS 4 Angstroem / CH₂Cl₂; toluene / 11 h / -20 °C

4: 91 percent / Red-al / toluene; tetrahydrofuran / 10.2 h / 0 °C

5: 93 percent / triethylamine, 4-DMAP / CH₂Cl₂ / 4 h / Ambient temperature

6: sodium hydride / tetrahydrofuran; dimethylformamide / 5 h / Ambient temperature

7: sodium bromide / dimethylformamide / 48 h / Ambient temperature

8: Mg / tetrahydrofuran / 1 h / Irradiation

9: CuI / tetrahydrofuran

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; (-)-diisopropyl tartrate; MS 4 Angstroem; sodium hydride; diisobutylaluminium hydride; magnesium; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium bromide; copper(l) iodide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4020(01)81547-7