methyl 3,7-anhydro-2,4,5,6-tetra-O-benzyl-8-deoxy-2-C-phenyl-L-threo-D-gulo-octonate

Base Information

Chemical Name:methyl 3,7-anhydro-2,4,5,6-tetra-O-benzyl-8-deoxy-2-C-phenyl-L-threo-D-gulo-octonate
CAS No.:740817-12-3
Molecular Formula:C₄₃H₄₄O₇
Molecular Weight:672.818
Hs Code.:

Synonyms:methyl 3,7-anhydro-2,4,5,6-tetra-O-benzyl-8-deoxy-2-C-phenyl-L-threo-D-gulo-octonate

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Chemical Property of methyl 3,7-anhydro-2,4,5,6-tetra-O-benzyl-8-deoxy-2-C-phenyl-L-threo-D-gulo-octonate

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Technology Process of methyl 3,7-anhydro-2,4,5,6-tetra-O-benzyl-8-deoxy-2-C-phenyl-L-threo-D-gulo-octonate

There total 11 articles about methyl 3,7-anhydro-2,4,5,6-tetra-O-benzyl-8-deoxy-2-C-phenyl-L-threo-D-gulo-octonate 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:

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

: 740817-12-3
methyl 3,7-anhydro-2,4,5,6-tetra-O-benzyl-8-deoxy-2-C-phenyl-L-threo-D-gulo-octonate

Guidance literature:: Multi-step reaction with 12 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: tetrahydrofuran; diethyl ether / 1.5 h / -60 - -35 °C

7.1: 225 mg / pyridinium chlorochromate / CH₂Cl₂ / 1 h / 20 °C

8.1: nBuLi / diethyl ether; hexane / 0.75 h / -78 - -75 °C

8.2: 75 percent / diethyl ether; hexane / 1.17 h / -75 - -65 °C

9.1: 123 mg / NaH / dimethylformamide / 3.5 h / 20 °C

10.1: methyl triflate / acetonitrile / 0.17 h / 20 °C

10.2: NaBH₄ / methanol / 0.75 h / 20 °C

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

11.1: CrO₃; H₂SO₄ / acetone; H₂O / 3.5 h / 0 - 20 °C

12.1: 32 mg / diethyl ether; methanol / 0.08 h / 0 °C

With chromium(VI) oxide; triethylsilane; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; sodium hydride; triethylamine; pyridinium chlorochromate; methyl trifluoromethanesulfonate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 11.1: Jones oxidation;
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

: 740817-12-3
methyl 3,7-anhydro-2,4,5,6-tetra-O-benzyl-8-deoxy-2-C-phenyl-L-threo-D-gulo-octonate

Guidance literature:: Multi-step reaction with 9 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: tetrahydrofuran; diethyl ether / 1.5 h / -60 - -35 °C

4.1: 225 mg / pyridinium chlorochromate / CH₂Cl₂ / 1 h / 20 °C

5.1: nBuLi / diethyl ether; hexane / 0.75 h / -78 - -75 °C

5.2: 75 percent / diethyl ether; hexane / 1.17 h / -75 - -65 °C

6.1: 123 mg / NaH / dimethylformamide / 3.5 h / 20 °C

7.1: methyl triflate / acetonitrile / 0.17 h / 20 °C

7.2: NaBH₄ / methanol / 0.75 h / 20 °C

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

8.1: CrO₃; H₂SO₄ / acetone; H₂O / 3.5 h / 0 - 20 °C

9.1: 32 mg / diethyl ether; methanol / 0.08 h / 0 °C

With chromium(VI) oxide; triethylsilane; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; sodium hydride; pyridinium chlorochromate; methyl trifluoromethanesulfonate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 8.1: Jones oxidation;
DOI:10.1021/jo049406a

Reference yield:

: phenylmagnesium bromide

: 740817-12-3
methyl 3,7-anhydro-2,4,5,6-tetra-O-benzyl-8-deoxy-2-C-phenyl-L-threo-D-gulo-octonate

Guidance literature:: Multi-step reaction with 7 steps

1.1: tetrahydrofuran; diethyl ether / 1.5 h / -60 - -35 °C

2.1: 225 mg / pyridinium chlorochromate / CH₂Cl₂ / 1 h / 20 °C

3.1: nBuLi / diethyl ether; hexane / 0.75 h / -78 - -75 °C

3.2: 75 percent / diethyl ether; hexane / 1.17 h / -75 - -65 °C

4.1: 123 mg / NaH / dimethylformamide / 3.5 h / 20 °C

5.1: methyl triflate / acetonitrile / 0.17 h / 20 °C

5.2: NaBH₄ / methanol / 0.75 h / 20 °C

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

6.1: CrO₃; H₂SO₄ / acetone; H₂O / 3.5 h / 0 - 20 °C

7.1: 32 mg / diethyl ether; methanol / 0.08 h / 0 °C

With chromium(VI) oxide; n-butyllithium; sulfuric acid; sodium hydride; pyridinium chlorochromate; methyl trifluoromethanesulfonate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 6.1: Jones oxidation;
DOI:10.1021/jo049406a