(S)-3-((2S,5R,6R)-5-(benzyloxy)-6-((tert-butyldimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)-2-methylpropane-1,2-diol

Base Information

• Chemical Name: (S)-3-((2S,5R,6R)-5-(benzyloxy)-6-((tert-butyldimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)-2-methylpropane-1,2-diol
• CAS No.: 1335029-08-7
• Molecular Formula: C₂₂H₃₈O₅Si
• Molecular Weight: 410.626

Synonyms:(S)-3-((2S,5R,6R)-5-(benzyloxy)-6-((tert-butyldimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)-2-methylpropane-1,2-diol

Chemical Property of (S)-3-((2S,5R,6R)-5-(benzyloxy)-6-((tert-butyldimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)-2-methylpropane-1,2-diol

Chemical Property:

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Safty Information:

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Useful:

Technology Process of (S)-3-((2S,5R,6R)-5-(benzyloxy)-6-((tert-butyldimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)-2-methylpropane-1,2-diol

There total 5 articles about (S)-3-((2S,5R,6R)-5-(benzyloxy)-6-((tert-butyldimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)-2-methylpropane-1,2-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: 83.0%

(((2R,3R,6S)-3-(benzyloxy)-6-(2-methylallyl)tetrahydro-2H-pyran-2-yl)oxy)(tert-butyl)dimethylsilane (1335028-93-7) → (S)-3-((2S,5R,6R)-5-(benzyloxy)-6-((tert-butyldimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)-2-methylpropane-1,2-diol (1335029-08-7) + (R)-3-((2S,5R,6R)-5-(benzyloxy)-6-((tert-butyldimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)-2-methylpropane-1,2-diol (1335028-94-8)

Guidance literature:

With AD-mix-β; water; In tert-butyl alcohol; at 0 ℃; for 24h; optical yield given as %de; diastereoselective reaction;

DOI:10.1002/anie.201101741

Reference yield:

(2R,5S)-2-(benzyloxy)-7-methyloct-7-ene-1,5-diol (1335028-91-5) → (S)-3-((2S,5R,6R)-5-(benzyloxy)-6-((tert-butyldimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)-2-methylpropane-1,2-diol (1335029-08-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 12 h

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 - -40 °C

2.2: 12 h / -40 - 25 °C

3.1: 1H-imidazole; dmap / dichloromethane / 3 h

4.1: AD-mix-β; water / tert-butyl alcohol / 24 h / 0 °C

With 1H-imidazole; dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; AD-mix-β; water; diisobutylaluminium hydride; In dichloromethane; toluene; tert-butyl alcohol; 4.1: Sharpless dihydroxylation;

DOI:10.1002/anie.201101741

Reference yield:

(7R)-7-(benzyloxy)-8-((4-methoxybenzyl)oxy)-2-methyloct-1-en-4-ol → (S)-3-((2S,5R,6R)-5-(benzyloxy)-6-((tert-butyldimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)-2-methylpropane-1,2-diol (1335029-08-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; tert-butyl alcohol / 2 h / 25 °C / pH 7 / aq. buffer

2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 12 h

3.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 - -40 °C

3.2: 12 h / -40 - 25 °C

4.1: 1H-imidazole; dmap / dichloromethane / 3 h

5.1: AD-mix-β; water / tert-butyl alcohol / 24 h / 0 °C

With 1H-imidazole; dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; AD-mix-β; water; diisobutylaluminium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; toluene; tert-butyl alcohol; 5.1: Sharpless dihydroxylation;

DOI:10.1002/anie.201101741

upstream raw materials:

(2R,5S)-2-(benzyloxy)-7-methyloct-7-ene-1,5-diol

(3R,6S)-3-(benzyloxy)-6-(2-methylallyl)tetrahydro-2H-pyran-2-one

(((2R,3R,6S)-3-(benzyloxy)-6-(2-methylallyl)tetrahydro-2H-pyran-2-yl)oxy)(tert-butyl)dimethylsilane

Downstream raw materials:

(2S,6R,8S,11R)-11-(benzyloxy)-2-((R)-1-((4-methoxybenzyl)oxy)propan-2-yl)-4-methyl-8-(((S)-2,2,4-trimethyl-1,3-dioxolan-4-yl)methyl)-1,7-dioxaspiro[5.5]undec-4-ene

(2S,5R,10S,11R)-5-(benzyloxy)-2-hydroxy-12-((4-methoxybenzyl)oxy)-11-methyl-10-((triethylsilyl)oxy)-1-((S)-2,2,4-trimethyl-1,3-dioxolan-4-yl)dodec-7-yn-6-one

(S)-2-((2S,6R,8S,11R)-11-(benzyloxy)-4-methyl-8-(((S)-2,2,4-trimethyl-1,3-dioxolan-4-yl)methyl)-1,7-dioxaspiro[5.5]undec-4-en-2-yl)propanal

(6R,E)-6-((2S,6R,8S,11R)-11-(benzyloxy)-4-methyl-8-(((S)-2,2,4-trimethyl-1,3-dioxolan-4-yl)methyl)-1,7-dioxaspiro[5.5]undec-4-en-2-yl)-1-((2S,4aR,6S,8R,8aR)-8-(benzyloxy)-6-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-2-methoxy-7-methyleneoctahydropyrano[3,2-b]pyran-2-yl)hept-4-en-3-one

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