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

Base Information

Chemical Name:(2S,3S,4R,5R,6R)-6-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-iodo-2,4-dimethyltetrahydro-2H-pyran-3-ol
CAS No.:1133161-30-4
Molecular Formula:C₂₀H₃₃IO₄Si
Molecular Weight:492.47
Hs Code.:

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

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

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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

There total 10 articles about (2S,3S,4R,5R,6R)-6-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-iodo-2,4-dimethyltetrahydro-2H-pyran-3-ol 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%

: 1310721-39-1
C₁₃H₂₆O₃Si

: 100-51-6,185532-71-2
benzyl alcohol

: 1133161-30-4
(2S,3S,4R,5R,6R)-6-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-iodo-2,4-dimethyltetrahydro-2H-pyran-3-ol

Guidance literature:: With N-iodo-succinimide; In dichloromethane; at -45 - -20 ℃; for 1h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1039/c1cc11448d

Reference yield: 77.0%

: 1133161-56-4
benzyl 4-O-acetyl-3-O-t-butyldimethylsilyl-2,6-dideoxy-2-iodo-3-C-methyl-α-L-mannopyranoside

: 1133161-30-4
(2S,3S,4R,5R,6R)-6-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-iodo-2,4-dimethyltetrahydro-2H-pyran-3-ol

Guidance literature:: benzyl 4-O-acetyl-3-O-t-butyldimethylsilyl-2,6-dideoxy-2-iodo-3-C-methyl-α-L-mannopyranoside; With diisobutylaluminium hydride; In dichloromethane; pentane; at -78 ℃; for 4.08333h; Inert atmosphere;

With methanol; rochelle salt; In dichloromethane; pentane; for 1h;
DOI:10.1021/jo900131a

Reference yield:

: 68673-58-5
(2S,3S)-3-hydroxy-2-methyl-2H-pyran-4(3H)-one

: 1133161-30-4
(2S,3S,4R,5R,6R)-6-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-iodo-2,4-dimethyltetrahydro-2H-pyran-3-ol

Guidance literature:: Multi-step reaction with 5 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

With dmap; N-iodo-succinimide; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; diethyl ether; n-heptane; dichloromethane; toluene;
DOI:10.1039/c1cc11448d