(1R,4R)-1-O-allyloxycarbonyl-1-(2,3,4,6-tetra-O-benzyl-D-gluco-β-C-pyranosyl)-4-O-(tert-butyldimethylsilyl)pent-2-yne-1,4-diol

Base Information

Chemical Name:(1R,4R)-1-O-allyloxycarbonyl-1-(2,3,4,6-tetra-O-benzyl-D-gluco-β-C-pyranosyl)-4-O-(tert-butyldimethylsilyl)pent-2-yne-1,4-diol
CAS No.:608530-10-5
Molecular Formula:C₄₉H₆₀O₉Si
Molecular Weight:821.096
Hs Code.:

Synonyms:(1R,4R)-1-O-allyloxycarbonyl-1-(2,3,4,6-tetra-O-benzyl-D-gluco-β-C-pyranosyl)-4-O-(tert-butyldimethylsilyl)pent-2-yne-1,4-diol

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Chemical Property of (1R,4R)-1-O-allyloxycarbonyl-1-(2,3,4,6-tetra-O-benzyl-D-gluco-β-C-pyranosyl)-4-O-(tert-butyldimethylsilyl)pent-2-yne-1,4-diol

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Technology Process of (1R,4R)-1-O-allyloxycarbonyl-1-(2,3,4,6-tetra-O-benzyl-D-gluco-β-C-pyranosyl)-4-O-(tert-butyldimethylsilyl)pent-2-yne-1,4-diol

There total 1 articles about (1R,4R)-1-O-allyloxycarbonyl-1-(2,3,4,6-tetra-O-benzyl-D-gluco-β-C-pyranosyl)-4-O-(tert-butyldimethylsilyl)pent-2-yne-1,4-diol 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%

: 2937-50-0
Allyl chloroformate

: 608529-93-7
(1R,4R)-1-(2,3,4,6-tetra-O-benzyl-D-gluco-β-C-pyranosyl)-4-O-(tert-butyldimethylsilyl)pent-2-yne-1,4-diol

: 608530-10-5
(1R,4R)-1-O-allyloxycarbonyl-1-(2,3,4,6-tetra-O-benzyl-D-gluco-β-C-pyranosyl)-4-O-(tert-butyldimethylsilyl)pent-2-yne-1,4-diol

Guidance literature:: With pyridine; In dichloromethane; at 0 - 20 ℃;
DOI:10.1002/ejoc.200300255

Reference yield: 92.0%

: 608530-10-5
(1R,4R)-1-O-allyloxycarbonyl-1-(2,3,4,6-tetra-O-benzyl-D-gluco-β-C-pyranosyl)-4-O-(tert-butyldimethylsilyl)pent-2-yne-1,4-diol

: 608530-11-6
(1R,4R)-1-O-allyloxycarbonyl-1-(2,3,4,6-tetra-O-benzyl-D-gluco-β-C-pyranosyl)pent-2-yne-1,4-diol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1002/ejoc.200300255

Reference yield:

: 608530-10-5
(1R,4R)-1-O-allyloxycarbonyl-1-(2,3,4,6-tetra-O-benzyl-D-gluco-β-C-pyranosyl)-4-O-(tert-butyldimethylsilyl)pent-2-yne-1,4-diol

: dimethyl (2S,3S)-2-methyl-3-[(E)-2-(2,3,4,6-tetra-O-benzyl-D-gluco-β-C-pyranosyl)ethenyl]cyclopropane-1,1-dicarboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 92 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C

2.1: 92 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

3.1: 83 percent / Pd(OAc)2; TPPTS; diethylamine / H₂O; acetonitrile / 20 °C

4.1: 70 percent / hydrogen; pyridine / Pd/C / methanol / 20 °C

5.1: NaH / tetrahydrofuran

5.2: 43 percent / Pd(OAc)2; bis(diphenylphosphanyl)ethane / tetrahydrofuran / 1 h / 20 °C

6.1: 71 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

7.1: 68 percent / DBU / Pd(OAc)2; bis(diphenylphosphanyl)ethane / tetrahydrofuran / 1 h / 20 °C

With pyridine; palladium diacetate; tetrabutyl ammonium fluoride; trisodium tris(3-sulfophenyl)phosphine; hydrogen; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; diethylamine; palladium diacetate; palladium on activated charcoal; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;
DOI:10.1002/ejoc.200300255