2,3,4,6-tetra-O-benzyl-1-O-(tert-butyldimethylsilyl)-5a-carba-β-D-xylo-hex-5(5a)-enopyranose

Base Information

Chemical Name:2,3,4,6-tetra-O-benzyl-1-O-(tert-butyldimethylsilyl)-5a-carba-β-D-xylo-hex-5(5a)-enopyranose
CAS No.:1147490-71-8
Molecular Formula:C₄₁H₅₀O₅Si
Molecular Weight:650.93
Hs Code.:

Synonyms:2,3,4,6-tetra-O-benzyl-1-O-(tert-butyldimethylsilyl)-5a-carba-β-D-xylo-hex-5(5a)-enopyranose

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Chemical Property of 2,3,4,6-tetra-O-benzyl-1-O-(tert-butyldimethylsilyl)-5a-carba-β-D-xylo-hex-5(5a)-enopyranose

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Technology Process of 2,3,4,6-tetra-O-benzyl-1-O-(tert-butyldimethylsilyl)-5a-carba-β-D-xylo-hex-5(5a)-enopyranose

There total 10 articles about 2,3,4,6-tetra-O-benzyl-1-O-(tert-butyldimethylsilyl)-5a-carba-β-D-xylo-hex-5(5a)-enopyranose 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: 95.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 99695-34-8
(1R,2S,3S,4R)-2,3,4-tri-O-benzyl-5-(benzyloxymethyl)-cyclohex-5-ene-1,2,3,4-tetrol

: 1147490-71-8
2,3,4,6-tetra-O-benzyl-1-O-(tert-butyldimethylsilyl)-5a-carba-β-D-xylo-hex-5(5a)-enopyranose

Guidance literature:: With 1H-imidazole; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 20h;
DOI:10.1016/j.carres.2008.12.023

Reference yield:

: 4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9
2,3,4,6-Tetra-O-benzyl-D-glucopyranose

: 1147490-71-8
2,3,4,6-tetra-O-benzyl-1-O-(tert-butyldimethylsilyl)-5a-carba-β-D-xylo-hex-5(5a)-enopyranose

Guidance literature:: Multi-step reaction with 6 steps

1.1: toluene; tetrahydrofuran / 3.67 h / 0 - 50 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.25 h / -78 - -40 °C / Inert atmosphere

2.2: 2.25 h / -78 - 20 °C

3.1: L-proline / dimethyl sulfoxide / 8 h / 50 °C

4.1: pyridine; trichlorophosphate / 0 - 20 °C

5.1: cerium(III) chloride heptahydrate / tetrahydrofuran; methanol / 0.5 h / -23 °C

5.2: 0.75 h

6.1: 1H-imidazole / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

6.2: 12 h / 40 °C

With pyridine; 1H-imidazole; oxalyl dichloride; cerium(III) chloride heptahydrate; dimethyl sulfoxide; L-proline; trichlorophosphate; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

Reference yield:

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 1147490-71-8
2,3,4,6-tetra-O-benzyl-1-O-(tert-butyldimethylsilyl)-5a-carba-β-D-xylo-hex-5(5a)-enopyranose

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

1.2: -78 - 0 °C

1.3: cooling with ice

2.1: sodium tetrahydroborate / tetrahydrofuran / 20 °C

3.1: trifluoroacetic anhydride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C

3.2: -78 - 0 °C

4.1: potassium carbonate / 18-crown-6 ether / toluene / 20 °C

5.1: cerium(III) chloride heptahydrate / tetrahydrofuran; methanol / 0.5 h / -23 °C

5.2: 0.75 h

6.1: 1H-imidazole / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

6.2: 12 h / 40 °C

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride heptahydrate; potassium carbonate; dimethyl sulfoxide; trifluoroacetic anhydride; 18-crown-6 ether; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;