phenyl 2,3-di-O-benzyl-6-deoxy-4-O-((S)-glycidyl)-1-thio-β-D-glucopyranoside

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Chemical Name:phenyl 2,3-di-O-benzyl-6-deoxy-4-O-((S)-glycidyl)-1-thio-β-D-glucopyranoside
CAS No.:868258-86-0
Molecular Formula:C₂₉H₃₂O₅S
Molecular Weight:492.636
Hs Code.:

Synonyms:phenyl 2,3-di-O-benzyl-6-deoxy-4-O-((S)-glycidyl)-1-thio-β-D-glucopyranoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of phenyl 2,3-di-O-benzyl-6-deoxy-4-O-((S)-glycidyl)-1-thio-β-D-glucopyranoside

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Technology Process of phenyl 2,3-di-O-benzyl-6-deoxy-4-O-((S)-glycidyl)-1-thio-β-D-glucopyranoside

There total 1 articles about phenyl 2,3-di-O-benzyl-6-deoxy-4-O-((S)-glycidyl)-1-thio-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: 60.0%

: 125085-03-2
phenyl 2,3-di-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside

: 70987-78-9,6746-81-2
(S)-Glycidyl tosylate

: 868258-86-0
phenyl 2,3-di-O-benzyl-6-deoxy-4-O-((S)-glycidyl)-1-thio-β-D-glucopyranoside

Guidance literature:: With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; for 24h;
DOI:10.1021/jm050368c

Reference yield:

: 868258-86-0
phenyl 2,3-di-O-benzyl-6-deoxy-4-O-((S)-glycidyl)-1-thio-β-D-glucopyranoside

: 6-O-(4-O-((S)-3-amino-2-hydroxypropyl)-6-deoxy-α-D-glucopyranosyl)neamine

Guidance literature:: Multi-step reaction with 6 steps

1.1: aq. Na₃N; CeCl₃ / acetonitrile / 24 h / Heating

2.1: DMAP; Et₃N / CH₂Cl₂ / 4 h / 20 °C

3.1: N-iodosuccinimide / diethyl ether; CH₂Cl₂ / -70 - -40 °C

3.2: trifluoromethanesulphonic acid / diethyl ether; CH₂Cl₂ / 4 h

4.1: MeONa / tetrahydrofuran; methanol / 2 h / 20 °C

5.1: PMe₃; aq. NaOH / tetrahydrofuran / 2 h / 50 °C

6.1: H₂; aq.AcOH / Pd(OH)2/C / 24 h / 20 °C / atmospheric pressure

With dmap; sodium hydroxide; N-iodo-succinimide; cerium(III) chloride; hydrogen; sodium methylate; acetic acid; triethylamine; trimethylphosphane; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile;
DOI:10.1021/jm050368c