methyl (2S,3R)-4-[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tertbutyldimethylsilyl)oxy]methyl}oxan-2-yl]-2,3-dihydroxybutanoate

Base Information

• Chemical Name: methyl (2S,3R)-4-[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tertbutyldimethylsilyl)oxy]methyl}oxan-2-yl]-2,3-dihydroxybutanoate
• CAS No.: 1391974-08-5
• Molecular Formula: C₃₇H₆₀O₉Si₂
• Molecular Weight: 705.049

Synonyms:

Chemical Property of methyl (2S,3R)-4-[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tertbutyldimethylsilyl)oxy]methyl}oxan-2-yl]-2,3-dihydroxybutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2S,3R)-4-[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tertbutyldimethylsilyl)oxy]methyl}oxan-2-yl]-2,3-dihydroxybutanoate

There total 8 articles about methyl (2S,3R)-4-[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tertbutyldimethylsilyl)oxy]methyl}oxan-2-yl]-2,3-dihydroxybutanoate 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:

methyl (2E)-4-[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]but-2-enoate (1391973-87-7) → methyl (2R,3S)-4-[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tertbutyldimethylsilyl)oxy]methyl}oxan-2-yl]-2,3-dihydroxybutanoate (1391974-09-6) + methyl (2S,3R)-4-[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tertbutyldimethylsilyl)oxy]methyl}oxan-2-yl]-2,3-dihydroxybutanoate (1391974-08-5)

Guidance literature:

With osmium(VIII) oxide; methanesulfonamide; potassium carbonate; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; potassium hexacyanoferrate(III); In tert-butyl alcohol; at 20 ℃; for 19h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1002/anie.201201826

Reference yield:

[(3aR,5R,6R,7S,7aS)-6,7-bis(benzyloxy)-2-(iodomethyl)-hexahydro-2H-furo[3,2-b]pyran-5-yl]methanol → methyl (2R,3S)-4-[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tertbutyldimethylsilyl)oxy]methyl}oxan-2-yl]-2,3-dihydroxybutanoate (1391974-09-6) + methyl (2S,3R)-4-[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tertbutyldimethylsilyl)oxy]methyl}oxan-2-yl]-2,3-dihydroxybutanoate (1391974-08-5)

Guidance literature:

Multi-step reaction with 4 steps

1: chloro-trimethyl-silane / tetrahydrofuran; water; ethylene dibromide / 1 h / 20 °C / Inert atmosphere

2: 1H-imidazole / N,N-dimethyl-formamide / 42 h / 20 °C / Inert atmosphere

3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 22 h / 60 °C / Inert atmosphere

4: osmium(VIII) oxide; methanesulfonamide; potassium carbonate; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; potassium hexacyanoferrate(III) / tert-butyl alcohol / 19 h / 20 °C / Inert atmosphere

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; osmium(VIII) oxide; chloro-trimethyl-silane; methanesulfonamide; potassium carbonate; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; potassium hexacyanoferrate(III); In tetrahydrofuran; water; ethylene dibromide; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 4: Sharpless dihydroxylation;

DOI:10.1002/anie.201201826

Reference yield:

(2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(hydroxymethyl)-2-(prop-2-en-1-yl)oxan-3-ol (1391973-90-2) → methyl (2R,3S)-4-[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tertbutyldimethylsilyl)oxy]methyl}oxan-2-yl]-2,3-dihydroxybutanoate (1391974-09-6) + methyl (2S,3R)-4-[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tertbutyldimethylsilyl)oxy]methyl}oxan-2-yl]-2,3-dihydroxybutanoate (1391974-08-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 42 h / 20 °C / Inert atmosphere

2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 22 h / 60 °C / Inert atmosphere

3: osmium(VIII) oxide; methanesulfonamide; potassium carbonate; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; potassium hexacyanoferrate(III) / tert-butyl alcohol / 19 h / 20 °C / Inert atmosphere

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; osmium(VIII) oxide; methanesulfonamide; potassium carbonate; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; potassium hexacyanoferrate(III); In N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 3: Sharpless dihydroxylation;

DOI:10.1002/anie.201201826

upstream raw materials:

D-Glucose

(2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(hydroxymethyl)-2-(prop-2-en-1-yl)oxan-3-ol

{[(2R,3R,4S,5S,6R)-3,4-bis(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-6-(prop-2-en-1-yl)oxan-2-yl]methoxy}(tert-butyl)dimethylsilane

methyl (2E)-4-[(2R,3S,4S,5R,6R)-4,5-bis(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxan-2-yl]but-2-enoate

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