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

Base Information

Chemical Name:tert-butyldimethylsilyl 2,3,4-tri-O-benzyl-6-deoxy-5a-carba-α-L-arabino-hex-5-enopyranoside
CAS No.:942155-69-3
Molecular Formula:C₃₄H₄₄O₄Si
Molecular Weight:544.806
Hs Code.:

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

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

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

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

: 942155-68-2
2D-(2,3/4,5)-2,3,4-tri-O-benzyl-5-O-(tert-butyldimethylsilyl)tetrahydroxycyclohexanone

: 942155-69-3
tert-butyldimethylsilyl 2,3,4-tri-O-benzyl-6-deoxy-5a-carba-α-L-arabino-hex-5-enopyranoside

Guidance literature:: With pyridine; In tetrahydrofuran; at -40 - 20 ℃; for 1h;
DOI:10.1016/j.tetlet.2007.03.074

Reference yield: 88.0%

: 942155-68-2
2D-(2,3/4,5)-2,3,4-tri-O-benzyl-5-O-(tert-butyldimethylsilyl)tetrahydroxycyclohexanone

: Tebbe's reagent

: 942155-69-3
tert-butyldimethylsilyl 2,3,4-tri-O-benzyl-6-deoxy-5a-carba-α-L-arabino-hex-5-enopyranoside

Guidance literature:: With pyridine; In tetrahydrofuran; toluene; at -40 - 20 ℃;
DOI:10.1016/j.bmc.2009.07.025

Reference yield:

: (3R,4S,5R)-3,4,5-tris(benzyloxy)-2-methoxy-6-methylenetetrahydro-2H-pyran

: 942155-69-3
tert-butyldimethylsilyl 2,3,4-tri-O-benzyl-6-deoxy-5a-carba-α-L-arabino-hex-5-enopyranoside

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 88 percent / pyridine / tetrahydrofuran / 1 h / -40 - 20 °C

With pyridine; 2,6-dimethylpyridine; water; palladium dichloride; In tetrahydrofuran; 1,4-dioxane; dichloromethane;
DOI:10.1016/j.tetlet.2007.03.074