(2S,3S,4S,5S,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-tetrahydro-4H-pyran-4-ol

Base Information

• Chemical Name: (2S,3S,4S,5S,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-tetrahydro-4H-pyran-4-ol
• CAS No.: 948036-04-2
• Molecular Formula: C₂₉H₄₂O₆Si
• Molecular Weight: 514.734
• Mol file: 948036-04-2.mol

Synonyms:(2S,3S,4S,5S,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-tetrahydro-4H-pyran-4-ol

Chemical Property of (2S,3S,4S,5S,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-tetrahydro-4H-pyran-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S,5S,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-tetrahydro-4H-pyran-4-ol

There total 1 articles about (2S,3S,4S,5S,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-tetrahydro-4H-pyran-4-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: 88.0%

tert-butyldimethylsilyl chloride (18162-48-6) + allyl 2,4-di-O-benzyl-α-D-mannopyranoside (97576-59-5) → (2S,3S,4S,5S,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-tetrahydro-4H-pyran-4-ol (948036-04-2)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2007.06.057 DOI:10.1016/j.tet.2008.06.068

Reference yield: 93.0%

(2S,3S,4S,5S,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-tetrahydro-4H-pyran-4-ol (948036-04-2) + trifluoromethylsulfonic anhydride (358-23-6) → (2S,3S,4S,5R,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-4-trifluoromethanesulfonyloxy-tetrahydro-4H-pyran (948036-05-3)

Guidance literature:

With pyridine; at -20 - 20 ℃; for 2.5h;

DOI:10.1016/j.tetlet.2007.06.057

Reference yield:

(2S,3S,4S,5S,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-tetrahydro-4H-pyran-4-ol (948036-04-2) → 2,3,4-tri-O-benzyl-6-O-tert-butyldimethylsilyl-1-C-vinyl-D-altropyranose (948036-11-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 93 percent / pyridine / 2.5 h / -20 - 20 °C

2.1: 62 percent / 18-crown-6 / toluene / 24 h / 30 °C / sonication

3.1: 95 percent / NaOMe / methanol / 20 °C

4.1: 96 percent / NaH / dimethylformamide / 0 - 20 °C

5.1: PdCl₂ / acetate buffer / 4 h / 30 °C / sonication

5.2: DMSO; Ac₂O / 20 °C

6.1: 62 percent / CeCl₃ / toluene / 1 h / -78 °C

With pyridine; cerium(III) chloride; 18-crown-6 ether; sodium methylate; sodium hydride; palladium dichloride; In methanol; acetate buffer; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tetlet.2007.06.057

upstream raw materials:

tert-butyldimethylsilyl chloride

allyl 2,4-di-O-benzyl-α-D-mannopyranoside

Downstream raw materials:

(2S,3S,4S,5R,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-4-trifluoromethanesulfonyloxy-tetrahydro-4H-pyran

2,3,4-tri-O-benzyl-6-O-tert-butyldimethylsilyl-1-C-vinyl-D-altropyranose

(1R,2R,3R,4S,5R)-2,3,4-tris(benzyloxy)-5-vinyl-6,8-dioxabicyclo[3.2.1]octane

(2S,3S,4R,5R,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-tetrahydro-4H-pyran-4-yl acetate