(3E)-7-O-benzyl-2-O-[(tert-butyl)dimethylsilyl]-1,3,4-trideoxy-5,6-O-isopropylidene-D-erythro-hept-1,3-dienitol

Base Information

Chemical Name:(3E)-7-O-benzyl-2-O-[(tert-butyl)dimethylsilyl]-1,3,4-trideoxy-5,6-O-isopropylidene-D-erythro-hept-1,3-dienitol
CAS No.:287119-12-4
Molecular Formula:C₂₃H₃₆O₄Si
Molecular Weight:404.622
Hs Code.:

Synonyms:(3E)-7-O-benzyl-2-O-[(tert-butyl)dimethylsilyl]-1,3,4-trideoxy-5,6-O-isopropylidene-D-erythro-hept-1,3-dienitol

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Chemical Property of (3E)-7-O-benzyl-2-O-[(tert-butyl)dimethylsilyl]-1,3,4-trideoxy-5,6-O-isopropylidene-D-erythro-hept-1,3-dienitol

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Technology Process of (3E)-7-O-benzyl-2-O-[(tert-butyl)dimethylsilyl]-1,3,4-trideoxy-5,6-O-isopropylidene-D-erythro-hept-1,3-dienitol

There total 6 articles about (3E)-7-O-benzyl-2-O-[(tert-butyl)dimethylsilyl]-1,3,4-trideoxy-5,6-O-isopropylidene-D-erythro-hept-1,3-dienitol 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%

: 69739-34-0
t-butyldimethylsiyl triflate

: 287119-11-3
(3E)-7-O-benzyl-1,3,4-trideoxy-5,6-O-isopropylidene-D-erythro-hept-3-en-2-ulose

: 287119-12-4
(3E)-7-O-benzyl-2-O-[(tert-butyl)dimethylsilyl]-1,3,4-trideoxy-5,6-O-isopropylidene-D-erythro-hept-1,3-dienitol

Guidance literature:: With triethylamine; In diethyl ether; at 0 ℃; for 0.25h;
DOI:10.1002/(SICI)1522-2675(20000510)83:5<943::AID-HLCA943>3.0.CO;2-H

Reference yield:

: 3969-61-7
2,3,5,6-di-isopropyIidene-1,4-dihydroxy-D-mannitol

: 287119-12-4
(3E)-7-O-benzyl-2-O-[(tert-butyl)dimethylsilyl]-1,3,4-trideoxy-5,6-O-isopropylidene-D-erythro-hept-1,3-dienitol

Guidance literature:: Multi-step reaction with 4 steps

1: 78 percent / Ag₂O; Bu₄NI / ethyl acetate / 20 °C

2: 80 percent / H₅IO₆; NaIO₄ / methanol; H₂O / 24 h / 20 °C

3: 83 percent / tetrahydrofuran / 20 °C

4: 98 percent / Et₃N / diethyl ether / 0.25 h / 0 °C

With sodium periodate; tetra-(n-butyl)ammonium iodide; periodic acid; triethylamine; silver(l) oxide; In tetrahydrofuran; methanol; diethyl ether; water; ethyl acetate; 1: Etherification / 2: Oxidation / 3: Condensation / 4: Etherification;
DOI:10.1002/(SICI)1522-2675(20000510)83:5<943::AID-HLCA943>3.0.CO;2-H

Reference yield:

: 100-39-0
benzyl bromide

: 287119-12-4
(3E)-7-O-benzyl-2-O-[(tert-butyl)dimethylsilyl]-1,3,4-trideoxy-5,6-O-isopropylidene-D-erythro-hept-1,3-dienitol

Guidance literature:: Multi-step reaction with 4 steps

1: 78 percent / Ag₂O; Bu₄NI / ethyl acetate / 20 °C

2: 80 percent / H₅IO₆; NaIO₄ / methanol; H₂O / 24 h / 20 °C

3: 83 percent / tetrahydrofuran / 20 °C

4: 98 percent / Et₃N / diethyl ether / 0.25 h / 0 °C

With sodium periodate; tetra-(n-butyl)ammonium iodide; periodic acid; triethylamine; silver(l) oxide; In tetrahydrofuran; methanol; diethyl ether; water; ethyl acetate; 1: Etherification / 2: Oxidation / 3: Condensation / 4: Etherification;
DOI:10.1002/(SICI)1522-2675(20000510)83:5<943::AID-HLCA943>3.0.CO;2-H