(Z)-8,12-anhydro-9,10,11-tri-O-benzyl-6,7,13-trideoxy-1,2:3,4-di-O-isopropylidene-α-L-glycero-D-manno-D-galacto-tridec-6-eno-1,5-pyranose

Base Information

Chemical Name:(Z)-8,12-anhydro-9,10,11-tri-O-benzyl-6,7,13-trideoxy-1,2:3,4-di-O-isopropylidene-α-L-glycero-D-manno-D-galacto-tridec-6-eno-1,5-pyranose
CAS No.:740816-93-7
Molecular Formula:C₄₀H₄₈O₉
Molecular Weight:672.816
Hs Code.:

Synonyms:(Z)-8,12-anhydro-9,10,11-tri-O-benzyl-6,7,13-trideoxy-1,2:3,4-di-O-isopropylidene-α-L-glycero-D-manno-D-galacto-tridec-6-eno-1,5-pyranose

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Chemical Property of (Z)-8,12-anhydro-9,10,11-tri-O-benzyl-6,7,13-trideoxy-1,2:3,4-di-O-isopropylidene-α-L-glycero-D-manno-D-galacto-tridec-6-eno-1,5-pyranose

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Technology Process of (Z)-8,12-anhydro-9,10,11-tri-O-benzyl-6,7,13-trideoxy-1,2:3,4-di-O-isopropylidene-α-L-glycero-D-manno-D-galacto-tridec-6-eno-1,5-pyranose

There total 5 articles about (Z)-8,12-anhydro-9,10,11-tri-O-benzyl-6,7,13-trideoxy-1,2:3,4-di-O-isopropylidene-α-L-glycero-D-manno-D-galacto-tridec-6-eno-1,5-pyranose 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: 57.0%

: 69204-28-0
6-deoxy-1,2:3,4-di-O-isopropylidene-6-(triphenylphosphino)-α-D-galactopyranose iodide

: 740817-19-0
2,6-anhydro-3,4,5-tri-O-benzyl-7-deoxy-aldehydo-L-glycero-D-manno-heptose

: 740816-93-7
(Z)-8,12-anhydro-9,10,11-tri-O-benzyl-6,7,13-trideoxy-1,2:3,4-di-O-isopropylidene-α-L-glycero-D-manno-D-galacto-tridec-6-eno-1,5-pyranose

Guidance literature:: 6-deoxy-1,2:3,4-di-O-isopropylidene-6-(triphenylphosphino)-α-D-galactopyranose iodide; With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -30 ℃; for 0.0833333h;

2,6-anhydro-3,4,5-tri-O-benzyl-7-deoxy-aldehydo-L-glycero-D-manno-heptose; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -30 - -10 ℃; for 2h;
DOI:10.1021/jo049406a

Reference yield:

: 162118-38-9
(3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol

: 740816-93-7
(Z)-8,12-anhydro-9,10,11-tri-O-benzyl-6,7,13-trideoxy-1,2:3,4-di-O-isopropylidene-α-L-glycero-D-manno-D-galacto-tridec-6-eno-1,5-pyranose

Guidance literature:: Multi-step reaction with 6 steps

1.1: 97 percent / pyridinium chlorochromate

2.1: nBuLi / diethyl ether; hexane / 1 h / -78 - -75 °C

2.2: 93 percent / diethyl ether; hexane / 1.5 h / -75 - -65 °C

3.1: 93 percent / triethylamine / CH₂Cl₂ / 42 h / 20 °C

4.1: 95 percent / triethylsilane; trimethylsilyl triflate / CH₂Cl₂ / 1 h / 20 °C

5.1: methyl triflate / acetonitrile / 0.25 h / 20 °C

5.2: NaBH₄ / methanol / 0.17 h / 20 °C

5.3: AgNO₃; H₂O / acetonitrile / 0.17 h / 20 °C

6.1: n-butyllithium / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 0.08 h / -30 °C

6.2: 57 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 2 h / -30 - -10 °C

With triethylsilane; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; triethylamine; pyridinium chlorochromate; methyl trifluoromethanesulfonate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; acetonitrile; 6.2: Wittig reaction;
DOI:10.1021/jo049406a

Reference yield:

: 740816-90-4
2,3,4-tri-O-benzyl-1-C-(2-thiazolyl)-L-fucopyranose

: 740816-93-7
(Z)-8,12-anhydro-9,10,11-tri-O-benzyl-6,7,13-trideoxy-1,2:3,4-di-O-isopropylidene-α-L-glycero-D-manno-D-galacto-tridec-6-eno-1,5-pyranose

Guidance literature:: Multi-step reaction with 4 steps

1.1: 93 percent / triethylamine / CH₂Cl₂ / 42 h / 20 °C

2.1: 95 percent / triethylsilane; trimethylsilyl triflate / CH₂Cl₂ / 1 h / 20 °C

3.1: methyl triflate / acetonitrile / 0.25 h / 20 °C

3.2: NaBH₄ / methanol / 0.17 h / 20 °C

3.3: AgNO₃; H₂O / acetonitrile / 0.17 h / 20 °C

4.1: n-butyllithium / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 0.08 h / -30 °C

4.2: 57 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 2 h / -30 - -10 °C

With triethylsilane; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; triethylamine; methyl trifluoromethanesulfonate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; acetonitrile; 4.2: Wittig reaction;
DOI:10.1021/jo049406a