2D-(2,3/4,5)-2,3,4-tri-O-benzyl-5-O-(tert-butyldimethylsilyl)tetrahydroxycyclohexanone

Base Information

• Chemical Name: 2D-(2,3/4,5)-2,3,4-tri-O-benzyl-5-O-(tert-butyldimethylsilyl)tetrahydroxycyclohexanone
• CAS No.: 942155-68-2
• Molecular Formula: C₃₃H₄₂O₅Si
• Molecular Weight: 546.779

Synonyms:2D-(2,3/4,5)-2,3,4-tri-O-benzyl-5-O-(tert-butyldimethylsilyl)tetrahydroxycyclohexanone

Chemical Property of 2D-(2,3/4,5)-2,3,4-tri-O-benzyl-5-O-(tert-butyldimethylsilyl)tetrahydroxycyclohexanone

Chemical Property:

Purity/Quality:

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Technology Process of 2D-(2,3/4,5)-2,3,4-tri-O-benzyl-5-O-(tert-butyldimethylsilyl)tetrahydroxycyclohexanone

There total 2 articles about 2D-(2,3/4,5)-2,3,4-tri-O-benzyl-5-O-(tert-butyldimethylsilyl)tetrahydroxycyclohexanone 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: 89.0%

t-butyldimethylsiyl triflate (69739-34-0) + (2R,3R,4S,5S)-2,3,4-Tris-benzyloxy-5-hydroxy-cyclohexanone (174851-25-3) → 2D-(2,3/4,5)-2,3,4-tri-O-benzyl-5-O-(tert-butyldimethylsilyl)tetrahydroxycyclohexanone (942155-68-2)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -20 ℃; for 1h;

DOI:10.1016/j.bmc.2009.07.025

Reference yield:

(3R,4S,5R)-3,4,5-tris(benzyloxy)-2-methoxy-6-methylenetetrahydro-2H-pyran → 2D-(2,3/4,5)-2,3,4-tri-O-benzyl-5-O-(tert-butyldimethylsilyl)tetrahydroxycyclohexanone (942155-68-2)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂O / PdCl₂ / dioxane / 3 h / 60 °C

2: 2,6-lutidine / CH₂Cl₂ / 1 h / -20 °C

With 2,6-dimethylpyridine; water; palladium dichloride; In 1,4-dioxane; dichloromethane;

DOI:10.1016/j.tetlet.2007.03.074

Reference yield: 89.0%

2D-(2,3/4,5)-2,3,4-tri-O-benzyl-5-O-(tert-butyldimethylsilyl)tetrahydroxycyclohexanone (942155-68-2) → 1D-(1,2,3/4,5)-2,3,4-tri-O-benzyl-5-O-(tert-butyldimethsilyl)cyclohexanepentol (1191953-73-7)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 0 - 20 ℃; for 1h;

DOI:10.1016/j.bmc.2009.07.025

upstream raw materials:

t-butyldimethylsiyl triflate

(2R,3R,4S,5S)-2,3,4-Tris-benzyloxy-5-hydroxy-cyclohexanone

Downstream raw materials:

tert-butyldimethylsilyl 2,3,4-tri-O-benzyl-6-deoxy-5a-carba-α-L-arabino-hex-5-enopyranoside

(1S,2S,3S,4S,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexan-1-ol

tert-butyldimethylsilyl 2,3,4,6-tetra-O-benzyl-5a-carba-α-D-galactopyranoside

(2S,3S,4R)-1-O-(2,3,4,6-tetra-O-benzyl-5a-carba-α-D-galactopyranosyl)-2-N-benzylamino-3,4-O-isopropylideneoctadecane-1,3,4-triol

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