3,7-anhydro-4,5,6-tri-O-benzyl-8-deoxy-2-C-phenyl-aldehydo-L-threo-D-ido-octose

Base Information

Chemical Name:3,7-anhydro-4,5,6-tri-O-benzyl-8-deoxy-2-C-phenyl-aldehydo-L-threo-D-ido-octose
CAS No.:740817-16-7
Molecular Formula:C₃₅H₃₆O₆
Molecular Weight:552.667
Hs Code.:

Synonyms:3,7-anhydro-4,5,6-tri-O-benzyl-8-deoxy-2-C-phenyl-aldehydo-L-threo-D-ido-octose

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Chemical Property of 3,7-anhydro-4,5,6-tri-O-benzyl-8-deoxy-2-C-phenyl-aldehydo-L-threo-D-ido-octose

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Technology Process of 3,7-anhydro-4,5,6-tri-O-benzyl-8-deoxy-2-C-phenyl-aldehydo-L-threo-D-ido-octose

There total 6 articles about 3,7-anhydro-4,5,6-tri-O-benzyl-8-deoxy-2-C-phenyl-aldehydo-L-threo-D-ido-octose 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: 81.0%

: 740817-14-5
(1S)-2,6-anhydro-3,4,5-tri-O-benzyl-7-deoxy-1-C-phenyl-1-C-(2-thiazolyl)-L-glycero-D-manno-heptitol

: 740817-16-7
3,7-anhydro-4,5,6-tri-O-benzyl-8-deoxy-2-C-phenyl-aldehydo-L-threo-D-ido-octose

Guidance literature:: (1S)-2,6-anhydro-3,4,5-tri-O-benzyl-7-deoxy-1-C-phenyl-1-C-(2-thiazolyl)-L-glycero-D-manno-heptitol; With methyl trifluoromethanesulfonate; In dichloromethane; acetonitrile; at 20 ℃; for 0.25h;

With sodium tetrahydroborate; In ethanol; at 20 ℃; for 0.25h;

With water; silver nitrate; In dichloromethane; acetonitrile; at 20 ℃; for 0.25h;
DOI:10.1021/jo049406a

Reference yield:

: 144668-21-3
(3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one

: 740817-16-7
3,7-anhydro-4,5,6-tri-O-benzyl-8-deoxy-2-C-phenyl-aldehydo-L-threo-D-ido-octose

Guidance literature:: Multi-step reaction with 7 steps

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

1.2: 93 percent / diethyl ether; hexane / 1.5 h / -75 - -65 °C

2.1: 93 percent / triethylamine / CH₂Cl₂ / 42 h / 20 °C

3.1: 95 percent / triethylsilane; trimethylsilyl triflate / CH₂Cl₂ / 1 h / 20 °C

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

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

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

5.1: CH₂Cl₂ / 48 h / 20 °C

5.2: 72 percent / DMSO; acetic anhydride / 50 h / 20 °C

6.1: 99 percent / tetrahydrofuran; diethyl ether / 2 h / -50 - -30 °C

7.1: methyl triflate / acetonitrile; CH₂Cl₂ / 0.25 h / 20 °C

7.2: NaBH₄ / ethanol / 0.25 h / 20 °C

7.3: 81 percent / AgNO₃; H₂O / acetonitrile; CH₂Cl₂ / 0.25 h / 20 °C

With triethylsilane; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; triethylamine; methyl trifluoromethanesulfonate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetonitrile;
DOI:10.1021/jo049406a

Reference yield:

: 740817-18-9
1-O-acetyl-2,3,4-tri-O-benzyl-1-C-(2-thiazolyl)-α-L-fucopyranose

: 740817-16-7
3,7-anhydro-4,5,6-tri-O-benzyl-8-deoxy-2-C-phenyl-aldehydo-L-threo-D-ido-octose

Guidance literature:: Multi-step reaction with 5 steps

1.1: 95 percent / triethylsilane; trimethylsilyl triflate / CH₂Cl₂ / 1 h / 20 °C

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

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

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

3.1: CH₂Cl₂ / 48 h / 20 °C

3.2: 72 percent / DMSO; acetic anhydride / 50 h / 20 °C

4.1: 99 percent / tetrahydrofuran; diethyl ether / 2 h / -50 - -30 °C

5.1: methyl triflate / acetonitrile; CH₂Cl₂ / 0.25 h / 20 °C

5.2: NaBH₄ / ethanol / 0.25 h / 20 °C

5.3: 81 percent / AgNO₃; H₂O / acetonitrile; CH₂Cl₂ / 0.25 h / 20 °C

With triethylsilane; trimethylsilyl trifluoromethanesulfonate; methyl trifluoromethanesulfonate; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;
DOI:10.1021/jo049406a