2,6-anhydro-3,4,5-tri-O-benzyl-7-deoxy-1-C-(2-thiazolyl)-aldehydo-L-glycero-D-manno-heptose

Base Information

Chemical Name:2,6-anhydro-3,4,5-tri-O-benzyl-7-deoxy-1-C-(2-thiazolyl)-aldehydo-L-glycero-D-manno-heptose
CAS No.:740817-13-4
Molecular Formula:C₃₁H₃₁NO₅S
Molecular Weight:529.657
Hs Code.:

Synonyms:2,6-anhydro-3,4,5-tri-O-benzyl-7-deoxy-1-C-(2-thiazolyl)-aldehydo-L-glycero-D-manno-heptose

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Chemical Property of 2,6-anhydro-3,4,5-tri-O-benzyl-7-deoxy-1-C-(2-thiazolyl)-aldehydo-L-glycero-D-manno-heptose

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Technology Process of 2,6-anhydro-3,4,5-tri-O-benzyl-7-deoxy-1-C-(2-thiazolyl)-aldehydo-L-glycero-D-manno-heptose

There total 11 articles about 2,6-anhydro-3,4,5-tri-O-benzyl-7-deoxy-1-C-(2-thiazolyl)-aldehydo-L-glycero-D-manno-heptose 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: 72.0%

: 79265-30-8
2-(trimethylsilyl)thiazole

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

: 740817-13-4
2,6-anhydro-3,4,5-tri-O-benzyl-7-deoxy-1-C-(2-thiazolyl)-aldehydo-L-glycero-D-manno-heptose

Guidance literature:: 2-(trimethylsilyl)thiazole; 2,6-anhydro-3,4,5-tri-O-benzyl-7-deoxy-aldehydo-L-glycero-D-manno-heptose; In dichloromethane; at 20 ℃; for 48h;

With acetic anhydride; dimethyl sulfoxide; at 20 ℃; for 50h;
DOI:10.1021/jo049406a

Reference yield:

: 869500-97-0
3-Methyl-2-thiazol-2-yl-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-2,3-dihydro-benzothiazole

: 740817-13-4
2,6-anhydro-3,4,5-tri-O-benzyl-7-deoxy-1-C-(2-thiazolyl)-aldehydo-L-glycero-D-manno-heptose

Guidance literature:: With water; mercury dichloride; In dichloromethane; acetonitrile; at 20 ℃; for 1h;
DOI:10.1021/jo051377w

Reference yield:

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

: 740817-13-4
2,6-anhydro-3,4,5-tri-O-benzyl-7-deoxy-1-C-(2-thiazolyl)-aldehydo-L-glycero-D-manno-heptose

Guidance literature:: Multi-step reaction with 7 steps

1.1: pyridinium chlorochromate

2.1: n-butyllithium / diethyl ether; hexane / 0.75 h / -70 °C

2.2: diethyl ether; hexane / 2.25 h / -70 - -50 °C

3.1: 1.02 g / triethylamine / CH₂Cl₂ / 48 h / 20 °C

4.1: 88 percent / trimethylsilyl trifluoromethanesulfonate; triethylsilane / CH₂Cl₂ / 1 h / 20 °C

5.1: 150 mg / acetonitrile / 0.25 h / 20 °C

6.1: ethylmagnesium bromide / diethyl ether; tetrahydrofuran / 2 h / 0 - 20 °C

6.2: tetrahydrofuran; diethyl ether / 0.5 h / 0 - 20 °C

7.1: 74 mg / H₂O; HgCl₂ / acetonitrile; CH₂Cl₂ / 1 h / 20 °C

With triethylsilane; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; ethylmagnesium bromide; water; triethylamine; pyridinium chlorochromate; mercury dichloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetonitrile;
DOI:10.1021/jo051377w