(1S)-1,4-anhydro-1-(cyclohex-1-en-1-yl)-1,2-dideoxy-3,5-di-O-(p-toluoyl)-D-erythro-pentitol

Base Information

Chemical Name:(1S)-1,4-anhydro-1-(cyclohex-1-en-1-yl)-1,2-dideoxy-3,5-di-O-(p-toluoyl)-D-erythro-pentitol
CAS No.:259801-12-2
Molecular Formula:C₂₇H₃₀O₅
Molecular Weight:434.532
Hs Code.:

Synonyms:(1S)-1,4-anhydro-1-(cyclohex-1-en-1-yl)-1,2-dideoxy-3,5-di-O-(p-toluoyl)-D-erythro-pentitol

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Chemical Property of (1S)-1,4-anhydro-1-(cyclohex-1-en-1-yl)-1,2-dideoxy-3,5-di-O-(p-toluoyl)-D-erythro-pentitol

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Technology Process of (1S)-1,4-anhydro-1-(cyclohex-1-en-1-yl)-1,2-dideoxy-3,5-di-O-(p-toluoyl)-D-erythro-pentitol

There total 1 articles about (1S)-1,4-anhydro-1-(cyclohex-1-en-1-yl)-1,2-dideoxy-3,5-di-O-(p-toluoyl)-D-erythro-pentitol 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:

: 2044-08-8
1-bromocyclohex-1-ene

: 3601-89-6,4330-21-6,52304-86-6,3056-12-0,141846-57-3
Hoffer's chlorosugar

: 259801-12-2
(1S)-1,4-anhydro-1-(cyclohex-1-en-1-yl)-1,2-dideoxy-3,5-di-O-(p-toluoyl)-D-erythro-pentitol

Guidance literature:: 1-bromocyclohex-1-ene; With magnesium; ethylene dibromide; In tetrahydrofuran; at 50 ℃; for 2h;

With zinc(II) chloride; In tetrahydrofuran; for 2h; Heating;

Hoffer's chlorosugar; In tetrahydrofuran; at 20 ℃; for 16h;
DOI:10.1002/(SICI)1522-2675(19991215)82:12<2160::AID-HLCA2160>3.0.CO;2-4

Reference yield: 80.0%

: 259801-12-2
(1S)-1,4-anhydro-1-(cyclohex-1-en-1-yl)-1,2-dideoxy-3,5-di-O-(p-toluoyl)-D-erythro-pentitol

: 259801-16-6
(1S)-1,4-anhydro-1-(cyclohex-1-en-1-yl)-1,2-dideoxy-D-erythro-pentitol

Guidance literature:: With sodium methylate; In methanol; dichloromethane; at 20 ℃; for 4h;
DOI:10.1002/(SICI)1522-2675(19991215)82:12<2160::AID-HLCA2160>3.0.CO;2-4

Reference yield:

: 259801-12-2
(1S)-1,4-anhydro-1-(cyclohex-1-en-1-yl)-1,2-dideoxy-3,5-di-O-(p-toluoyl)-D-erythro-pentitol

: (1S)-1,4-anhydro-1-(cyclohex-1-en-1-yl)-1,2-dideoxy-5-O-(4,4'-dimethoxytrityl)-D-erythro-pentitol

Guidance literature:: Multi-step reaction with 2 steps

1: 80 percent / NaOMe / methanol; CH₂Cl₂ / 4 h / 20 °C

2: 85 percent / iPr₂EtN; 4-(dimethylamino)pyridine / pyridine; CH₂Cl₂ / 72 h / 20 °C

With dmap; sodium methylate; N-ethyl-N,N-diisopropylamine; In pyridine; methanol; dichloromethane; 1: Deacylation / 2: Etherification;
DOI:10.1002/(SICI)1522-2675(19991215)82:12<2160::AID-HLCA2160>3.0.CO;2-4