(2R,3R,4S,5R,6S)-5-acetoxy-6-((2S,3S,4R,5R,6R)-6-(benzyloxy)-4-(tertbutyldimethylsilyloxy)-5-iodo-2,4-dimethyltetrahydro-2H-pyran-3-yloxy)-4-methoxy-2-methyltetrahydro-2H-pyran-3-yl benzoate

Base Information

• Chemical Name: (2R,3R,4S,5R,6S)-5-acetoxy-6-((2S,3S,4R,5R,6R)-6-(benzyloxy)-4-(tertbutyldimethylsilyloxy)-5-iodo-2,4-dimethyltetrahydro-2H-pyran-3-yloxy)-4-methoxy-2-methyltetrahydro-2H-pyran-3-yl benzoate
• CAS No.: 1310721-45-9
• Molecular Formula: C₃₆H₅₁IO₁₀Si
• Molecular Weight: 798.785

Synonyms:

Chemical Property of (2R,3R,4S,5R,6S)-5-acetoxy-6-((2S,3S,4R,5R,6R)-6-(benzyloxy)-4-(tertbutyldimethylsilyloxy)-5-iodo-2,4-dimethyltetrahydro-2H-pyran-3-yloxy)-4-methoxy-2-methyltetrahydro-2H-pyran-3-yl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5R,6S)-5-acetoxy-6-((2S,3S,4R,5R,6R)-6-(benzyloxy)-4-(tertbutyldimethylsilyloxy)-5-iodo-2,4-dimethyltetrahydro-2H-pyran-3-yloxy)-4-methoxy-2-methyltetrahydro-2H-pyran-3-yl benzoate

There total 11 articles about (2R,3R,4S,5R,6S)-5-acetoxy-6-((2S,3S,4R,5R,6R)-6-(benzyloxy)-4-(tertbutyldimethylsilyloxy)-5-iodo-2,4-dimethyltetrahydro-2H-pyran-3-yloxy)-4-methoxy-2-methyltetrahydro-2H-pyran-3-yl benzoate 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:

(2S,3S,4R,5R,6R)-6-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-iodo-2,4-dimethyltetrahydro-2H-pyran-3-ol (1133161-30-4) + (2R,3R,4S,5R,6R)-5-acetoxy-4-methoxy-2-methyl-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3-yl benzoate (1310721-43-7) → (2R,3R,4S,5R,6S)-5-acetoxy-6-((2S,3S,4R,5R,6R)-6-(benzyloxy)-4-(tertbutyldimethylsilyloxy)-5-iodo-2,4-dimethyltetrahydro-2H-pyran-3-yloxy)-4-methoxy-2-methyltetrahydro-2H-pyran-3-yl benzoate (1310721-45-9) + (2R,3R,4S,5R,6R)-5-acetoxy-6-((2S,3S,4R,5R,6R)-6-(benzyloxy)-4-(tertbutyldimethylsilyloxy)-5-iodo-2,4-dimethyltetrahydro-2H-pyran-3-yloxy)-4-methoxy-2-methyltetrahydro-2H-pyran-3-yl benzoate

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -70 - -20 ℃; for 2.5h; optical yield given as %de; Molecular sieve; Inert atmosphere;

DOI:10.1039/c1cc11448d

Reference yield:

(2S,3S)-3-hydroxy-2-methyl-2H-pyran-4(3H)-one (68673-58-5) → (2R,3R,4S,5R,6S)-5-acetoxy-6-((2S,3S,4R,5R,6R)-6-(benzyloxy)-4-(tertbutyldimethylsilyloxy)-5-iodo-2,4-dimethyltetrahydro-2H-pyran-3-yloxy)-4-methoxy-2-methyltetrahydro-2H-pyran-3-yl benzoate (1310721-45-9) + (2R,3R,4S,5R,6R)-5-acetoxy-6-((2S,3S,4R,5R,6R)-6-(benzyloxy)-4-(tertbutyldimethylsilyloxy)-5-iodo-2,4-dimethyltetrahydro-2H-pyran-3-yloxy)-4-methoxy-2-methyltetrahydro-2H-pyran-3-yl benzoate

Guidance literature:

Multi-step reaction with 6 steps

1.1: tetrahydrofuran; diethyl ether; n-heptane; toluene / -78 °C / Inert atmosphere

1.2: 0.33 h / -78 °C / Inert atmosphere

2.1: dmap; triethylamine / dichloromethane / 15 h / 20 °C / Inert atmosphere

3.1: triethylamine / dichloromethane / 5 h / -78 - 20 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / tetrahydrofuran; dichloromethane / 0.5 h / -78 °C / Inert atmosphere

5.1: N-iodo-succinimide / dichloromethane / 1 h / -45 - -20 °C / Inert atmosphere

6.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2.5 h / -70 - -20 °C / Molecular sieve; Inert atmosphere

With dmap; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; diethyl ether; n-heptane; dichloromethane; toluene;

DOI:10.1039/c1cc11448d

Reference yield:

L-Rhamnose (3615-41-6,478518-52-4) → (2R,3R,4S,5R,6S)-5-acetoxy-6-((2S,3S,4R,5R,6R)-6-(benzyloxy)-4-(tertbutyldimethylsilyloxy)-5-iodo-2,4-dimethyltetrahydro-2H-pyran-3-yloxy)-4-methoxy-2-methyltetrahydro-2H-pyran-3-yl benzoate (1310721-45-9) + (2R,3R,4S,5R,6R)-5-acetoxy-6-((2S,3S,4R,5R,6R)-6-(benzyloxy)-4-(tertbutyldimethylsilyloxy)-5-iodo-2,4-dimethyltetrahydro-2H-pyran-3-yloxy)-4-methoxy-2-methyltetrahydro-2H-pyran-3-yl benzoate

Guidance literature:

Multi-step reaction with 9 steps

1.1: perchloric acid / 1.5 h / 40 °C / Inert atmosphere

1.2: 5 h / 23 °C / Inert atmosphere

1.3: 2 h / -20 - 0 °C / Inert atmosphere

2.1: methanol / 2.5 h / 20 °C / Inert atmosphere

3.1: dipyridinium dichromate; acetic acid / 48 h / 20 °C / Inert atmosphere

4.1: tetrahydrofuran; diethyl ether; n-heptane; toluene / -78 °C / Inert atmosphere

4.2: 0.33 h / -78 °C / Inert atmosphere

5.1: dmap; triethylamine / dichloromethane / 15 h / 20 °C / Inert atmosphere

6.1: triethylamine / dichloromethane / 5 h / -78 - 20 °C / Inert atmosphere

7.1: diisobutylaluminium hydride / tetrahydrofuran; dichloromethane / 0.5 h / -78 °C / Inert atmosphere

8.1: N-iodo-succinimide / dichloromethane / 1 h / -45 - -20 °C / Inert atmosphere

9.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2.5 h / -70 - -20 °C / Molecular sieve; Inert atmosphere

With methanol; dmap; N-iodo-succinimide; dipyridinium dichromate; perchloric acid; trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; acetic acid; triethylamine; In tetrahydrofuran; diethyl ether; n-heptane; dichloromethane; toluene;

DOI:10.1039/c1cc11448d

upstream raw materials:

(2S,3S,4R,5R,6R)-6-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-iodo-2,4-dimethyltetrahydro-2H-pyran-3-ol

(2R,3R,4S,5R,6R)-5-acetoxy-4-methoxy-2-methyl-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3-yl benzoate

4-O-acetyl-1,5-anhydro-3-O-t-butyldimethylsilyl-1,2,6-trideoxy-3-C-methyl-L-arabino-hex-1-enitol

C₁₃H₂₆O₃Si

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