tert-butyl 4-O-benzyl-2,3,6,7,8,9,10,11,12-nonadeoxy-α-D-threo-dodeca-8Z-enopyranoside

Base Information

Chemical Name:tert-butyl 4-O-benzyl-2,3,6,7,8,9,10,11,12-nonadeoxy-α-D-threo-dodeca-8Z-enopyranoside
CAS No.:167901-88-4
Molecular Formula:C₂₃H₃₆O₃
Molecular Weight:360.537
Hs Code.:

Synonyms:tert-butyl 4-O-benzyl-2,3,6,7,8,9,10,11,12-nonadeoxy-α-D-threo-dodeca-8Z-enopyranoside

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Chemical Property of tert-butyl 4-O-benzyl-2,3,6,7,8,9,10,11,12-nonadeoxy-α-D-threo-dodeca-8Z-enopyranoside

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Technology Process of tert-butyl 4-O-benzyl-2,3,6,7,8,9,10,11,12-nonadeoxy-α-D-threo-dodeca-8Z-enopyranoside

There total 2 articles about tert-butyl 4-O-benzyl-2,3,6,7,8,9,10,11,12-nonadeoxy-α-D-threo-dodeca-8Z-enopyranoside 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: 67.0%

: 1779-51-7
n-butyl(triphenyl)phosphonium bromide

: 321126-18-5
3-((2R,3R,6R)-3-Benzyloxy-6-tert-butoxy-tetrahydro-pyran-2-yl)-propionaldehyde

: 167901-88-4
tert-butyl 4-O-benzyl-2,3,6,7,8,9,10,11,12-nonadeoxy-α-D-threo-dodeca-8Z-enopyranoside

Guidance literature:: n-butyl(triphenyl)phosphonium bromide; With sodium hexamethyldisilazane; In hexane; toluene; at 20 ℃; for 1h;

3-((2R,3R,6R)-3-Benzyloxy-6-tert-butoxy-tetrahydro-pyran-2-yl)-propionaldehyde; In hexane; toluene; at -78 - 20 ℃;
DOI:10.1081/CAR-120014903

Reference yield:

: 167901-83-9
tert-butyl 4-O-benzyl-2,3,6,7,8,9-hexadeoxy-α-D-threo-non-8-enopyranoside

: 167901-88-4
tert-butyl 4-O-benzyl-2,3,6,7,8,9,10,11,12-nonadeoxy-α-D-threo-dodeca-8Z-enopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: O₃ / CH₂Cl₂; methanol / -78 °C

1.2: 80 percent / PPh₃ / CH₂Cl₂; methanol / 1 h / 20 °C

2.1: sodium bis(trimethylsilyl)amide / hexane; toluene / 1 h / 20 °C

2.2: 67 percent / hexane; toluene / -78 - 20 °C

With sodium hexamethyldisilazane; ozone; In methanol; hexane; dichloromethane; toluene; 2.1: Wittig reaction;
DOI:10.1081/CAR-120014903

Reference yield: 92.0%

: 167901-88-4
tert-butyl 4-O-benzyl-2,3,6,7,8,9,10,11,12-nonadeoxy-α-D-threo-dodeca-8Z-enopyranoside

: (2R,3R,6R)-3-Benzyloxy-6-tert-butoxy-2-[2-(3-propyl-oxiranyl)-ethyl]-tetrahydro-pyran

Guidance literature:: With disodium hydrogenphosphate; sodium dihydrogenphosphate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1081/CAR-120014903