2-(trimethylsilyl)ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

Chemical Name:2-(trimethylsilyl)ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
CAS No.:117253-02-8
Molecular Formula:C₃₃H₃₉NO₇Si
Molecular Weight:589.761
Hs Code.:

Synonyms:2-(trimethylsilyl)ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Chemical Property of 2-(trimethylsilyl)ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Technology Process of 2-(trimethylsilyl)ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 7 articles about 2-(trimethylsilyl)ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 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: 86.0%

: 117253-01-7
2-(trimethylsilyl)ethyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

: 117253-02-8
2-(trimethylsilyl)ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: With hydrogenchloride; 3 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.1021/jo00259a006

Reference yield: 78.0%

: 2916-68-9
2-(Trimethylsilyl)ethanol

: 115533-35-2
ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 117253-02-8
2-(trimethylsilyl)ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: 2-(Trimethylsilyl)ethanol; ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside; In dichloromethane; at 20 ℃; for 0.5h;

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1016/j.carres.2003.10.029

Reference yield:

: 187022-30-6
3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-α/β-D-glucopyranosyl chloride

: 117253-02-8
2-(trimethylsilyl)ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 64 percent / Hg(CN)2 / 1,2-dichloro-ethane / 1.) 70 deg C, 4 h, 2.) 50 deg C, 16 h

2: 96 percent / MeONa / methanol / 2.5 h / 22 °C

3: 91 percent / p-TsOH*H₂O / acetonitrile / 0.75 h

4: 1.) NaH / 1.) DMF, 2.) DMF, 22 deg C, 3 h

5: 86 percent / etheral HCl, NaCNBH₃, molecular sieves 3A / tetrahydrofuran / 1 h / 0 °C

With hydrogenchloride; 3 A molecular sieve; sodium methylate; mercury(II) cyanide; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; 1,2-dichloro-ethane; acetonitrile;
DOI:10.1021/jo00259a006