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

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Chemical Name:tert-butyldimethylsilyl 2,3,4,6-tetra-O-benzyl-5a-carba-α-D-galactopyranoside
CAS No.:942155-71-7
Molecular Formula:C₄₁H₅₂O₅Si
Molecular Weight:652.946
Hs Code.:

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

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

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

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

There total 5 articles about tert-butyldimethylsilyl 2,3,4,6-tetra-O-benzyl-5a-carba-α-D-galactopyranoside 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: 91.0%

: 942155-70-6
tert-butyldimethylsilyl 2,3,4-tri-O-benzyl-5a-carba-α-D-galactopyranoside

: 100-39-0
benzyl bromide

: 942155-71-7
tert-butyldimethylsilyl 2,3,4,6-tetra-O-benzyl-5a-carba-α-D-galactopyranoside

Guidance literature:: tert-butyldimethylsilyl 2,3,4-tri-O-benzyl-5a-carba-α-D-galactopyranoside; With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.5h;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil; at 0 - 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

: 942155-71-7
tert-butyldimethylsilyl 2,3,4,6-tetra-O-benzyl-5a-carba-α-D-galactopyranoside

Guidance literature:: Multi-step reaction with 5 steps

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

2.1: 2,6-lutidine / CH₂Cl₂ / 1 h / -20 °C

3.1: 88 percent / pyridine / tetrahydrofuran / 1 h / -40 - 20 °C

4.1: BH₃*THF / tetrahydrofuran / 2.5 h / 20 °C

4.2: 76 percent / aq. NaOH; aq. H₂O₂ / 1 h / 0 °C

5.1: NaH; (n-Bu)4NI / dimethylformamide; tetrahydrofuran / 12 h / 20 °C

With pyridine; 2,6-dimethylpyridine; borane-THF; water; tetra-(n-butyl)ammonium iodide; sodium hydride; palladium dichloride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2007.03.074

Reference yield:

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

: 942155-71-7
tert-butyldimethylsilyl 2,3,4,6-tetra-O-benzyl-5a-carba-α-D-galactopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 88 percent / pyridine / tetrahydrofuran / 1 h / -40 - 20 °C

2.1: BH₃*THF / tetrahydrofuran / 2.5 h / 20 °C

2.2: 76 percent / aq. NaOH; aq. H₂O₂ / 1 h / 0 °C

3.1: NaH; (n-Bu)4NI / dimethylformamide; tetrahydrofuran / 12 h / 20 °C

With pyridine; borane-THF; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2007.03.074