(1S)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-C-(2-thiazolyl)-1-C-trimethylsilylethynyl-D-glycero-D-gulo-heptitol

Base Information

Chemical Name:(1S)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-C-(2-thiazolyl)-1-C-trimethylsilylethynyl-D-glycero-D-gulo-heptitol
CAS No.:869500-84-5
Molecular Formula:C₄₃H₄₇NO₆SSi
Molecular Weight:734.001
Hs Code.:

Synonyms:(1S)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-C-(2-thiazolyl)-1-C-trimethylsilylethynyl-D-glycero-D-gulo-heptitol

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Chemical Property of (1S)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-C-(2-thiazolyl)-1-C-trimethylsilylethynyl-D-glycero-D-gulo-heptitol

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Technology Process of (1S)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-C-(2-thiazolyl)-1-C-trimethylsilylethynyl-D-glycero-D-gulo-heptitol

There total 4 articles about (1S)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-C-(2-thiazolyl)-1-C-trimethylsilylethynyl-D-glycero-D-gulo-heptitol 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: 61.0%

: 869500-66-3
2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-C-trimethylsilylethynyl-aldehydo-D-glycero-D-gulo-heptose

: 3034-53-5,215777-74-5
2-bromo-1,3-thiazole

: 869500-84-5
(1S)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-C-(2-thiazolyl)-1-C-trimethylsilylethynyl-D-glycero-D-gulo-heptitol

Guidance literature:: 2-bromo-1,3-thiazole; With n-butyllithium; In diethyl ether; hexane; at -78 - -75 ℃; for 0.75h;

2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-C-trimethylsilylethynyl-aldehydo-D-glycero-D-gulo-heptose; In diethyl ether; hexane; at -75 - -65 ℃; for 2.66h;
DOI:10.1021/jo051377w

Reference yield:

: 869500-98-1
3-Methyl-2-trimethylsilanylethynyl-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-2,3-dihydro-benzothiazole

: 869500-84-5
(1S)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-C-(2-thiazolyl)-1-C-trimethylsilylethynyl-D-glycero-D-gulo-heptitol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 281 mg / H₂O; HgCl₂ / acetonitrile; CH₂Cl₂ / 0.25 h / 20 °C

2.1: n-butyllithium / diethyl ether; hexane / 0.75 h / -78 - -75 °C

2.2: 61 percent / diethyl ether; hexane / 2.66 h / -75 - -65 °C

With n-butyllithium; water; mercury dichloride; In diethyl ether; hexane; dichloromethane; acetonitrile;
DOI:10.1021/jo051377w

Reference yield:

: 440677-66-7
2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)benzothiazole

: 869500-84-5
(1S)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-C-(2-thiazolyl)-1-C-trimethylsilylethynyl-D-glycero-D-gulo-heptitol

Guidance literature:: Multi-step reaction with 4 steps

1.1: acetonitrile / 0.25 h / 20 °C

2.1: ethylmagnesium bromide / diethyl ether; tetrahydrofuran / 1.25 h / 0 - 25 °C

2.2: tetrahydrofuran; diethyl ether / 0.75 h / 0 - 20 °C

3.1: 281 mg / H₂O; HgCl₂ / acetonitrile; CH₂Cl₂ / 0.25 h / 20 °C

4.1: n-butyllithium / diethyl ether; hexane / 0.75 h / -78 - -75 °C

4.2: 61 percent / diethyl ether; hexane / 2.66 h / -75 - -65 °C

With n-butyllithium; ethylmagnesium bromide; water; mercury dichloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetonitrile;
DOI:10.1021/jo051377w