ethyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-thio-β-D-fructofuranoside

Base Information

Chemical Name:ethyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-thio-β-D-fructofuranoside
CAS No.:302905-17-5
Molecular Formula:C₄₃H₆₆O₆SSi₃
Molecular Weight:795.316
Hs Code.:

Synonyms:ethyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-thio-β-D-fructofuranoside

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Chemical Property of ethyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-thio-β-D-fructofuranoside

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Technology Process of ethyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-thio-β-D-fructofuranoside

There total 6 articles about ethyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-thio-β-D-fructofuranoside 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: 98.0%

: 69304-37-6
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

: 302905-16-4
ethyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-thio-β-D-fructofuranoside

: 302905-17-5
ethyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-thio-β-D-fructofuranoside

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at -35 - 20 ℃; for 3h;
DOI:10.1021/ja001439u

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 302905-17-5
ethyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-thio-β-D-fructofuranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 74 percent / pyridine / 20 °C

2: 94 percent / pyridine; 4-(dimethylamino)pyridine / 4 h

3: 54 percent / aq. NaOH; Bu₄NHSO₄ / CH₂Cl₂ / 120 h / Heating

4: 80 percent / TFA; Et₃SiH / CH₂Cl₂; CHCl₃ / 2 h

5: 98 percent / imidazole / dimethylformamide / 3 h / -35 - 20 °C

With pyridine; 1H-imidazole; triethylsilane; dmap; sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; trifluoroacetic acid; In dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1021/ja001439u

Reference yield:

: 80763-61-7
ethyl 2-thio-β-D-fructofuranoside

: 302905-17-5
ethyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-thio-β-D-fructofuranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 74 percent / pyridine / 20 °C

2: 94 percent / pyridine; 4-(dimethylamino)pyridine / 4 h

3: 54 percent / aq. NaOH; Bu₄NHSO₄ / CH₂Cl₂ / 120 h / Heating

4: 80 percent / TFA; Et₃SiH / CH₂Cl₂; CHCl₃ / 2 h

5: 98 percent / imidazole / dimethylformamide / 3 h / -35 - 20 °C

With pyridine; 1H-imidazole; triethylsilane; dmap; sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; trifluoroacetic acid; In dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1021/ja001439u