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

Base Information

Chemical Name:(1S)-2,6-anhydro-3,4,5-tri-O-benzyl-7-deoxy-1-C-phenyl-1-C-(2-thiazolyl)-L-glycero-D-manno-heptitol
CAS No.:740817-14-5
Molecular Formula:C₃₇H₃₇NO₅S
Molecular Weight:607.77
Hs Code.:

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

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

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

There total 5 articles about (1S)-2,6-anhydro-3,4,5-tri-O-benzyl-7-deoxy-1-C-phenyl-1-C-(2-thiazolyl)-L-glycero-D-manno-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: 99.0%

: phenylmagnesium bromide

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

: 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

Guidance literature:: In tetrahydrofuran; diethyl ether; at -50 - -30 ℃; for 2h;
DOI:10.1021/jo049406a

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 6 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

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

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

Guidance literature:: Multi-step reaction with 4 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

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