(1R)-1,2-anhydro-3,5-dideoxy-1-ethenyl-4-O-{(3S)-3-[ (4-methoxybenzyl)oxy]pent-4-enoyl}-D-threopentitol

Base Information

Chemical Name:(1R)-1,2-anhydro-3,5-dideoxy-1-ethenyl-4-O-{(3S)-3-[ (4-methoxybenzyl)oxy]pent-4-enoyl}-D-threopentitol
CAS No.:1242065-84-4
Molecular Formula:C₂₀H₂₆O₅
Molecular Weight:346.423
Hs Code.:

Synonyms:(1R)-1,2-anhydro-3,5-dideoxy-1-ethenyl-4-O-{(3S)-3-[ (4-methoxybenzyl)oxy]pent-4-enoyl}-D-threopentitol

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Chemical Property of (1R)-1,2-anhydro-3,5-dideoxy-1-ethenyl-4-O-{(3S)-3-[ (4-methoxybenzyl)oxy]pent-4-enoyl}-D-threopentitol

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Technology Process of (1R)-1,2-anhydro-3,5-dideoxy-1-ethenyl-4-O-{(3S)-3-[ (4-methoxybenzyl)oxy]pent-4-enoyl}-D-threopentitol

There total 11 articles about (1R)-1,2-anhydro-3,5-dideoxy-1-ethenyl-4-O-{(3S)-3-[ (4-methoxybenzyl)oxy]pent-4-enoyl}-D-threopentitol 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: 83.0%

: 935475-92-6
(3S)-3-[(4-methoxybenzyl)oxy]-4-pentenoic acid

: 1240372-05-7
(1R)-1,2-anhydro-3,5-dideoxy-1-ethenyl-D-threopentitol

: 1242065-84-4
(1R)-1,2-anhydro-3,5-dideoxy-1-ethenyl-4-O-{(3S)-3-[ (4-methoxybenzyl)oxy]pent-4-enoyl}-D-threopentitol

Guidance literature:: (3S)-3-[(4-methoxybenzyl)oxy]-4-pentenoic acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

(1R)-1,2-anhydro-3,5-dideoxy-1-ethenyl-D-threopentitol; With dmap; In toluene; at 20 ℃; for 4h; Inert atmosphere;
DOI:10.1039/c004556j

Reference yield:

: 251571-56-9
[(S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-methanol

: 1242065-84-4
(1R)-1,2-anhydro-3,5-dideoxy-1-ethenyl-4-O-{(3S)-3-[ (4-methoxybenzyl)oxy]pent-4-enoyl}-D-threopentitol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 2 h / 25 °C / Inert atmosphere

2.1: tetrahydrofuran; hexane / 2 h / -10 - 25 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -15 °C / Inert atmosphere

4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 2 h / 25 °C / Inert atmosphere

5.1: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / tert-butyl alcohol; water / 6 h / 25 °C / Inert atmosphere

6.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

6.2: 10 h / Inert atmosphere

With dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; diisobutylaluminium hydride; dicyclohexyl-carbodiimide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; hexane; dichloromethane; water; dimethyl sulfoxide; toluene; tert-butyl alcohol; 2.1: |Wittig Olefination / 6.1: |Steglich Esterification / 6.2: |Steglich Esterification;
DOI:10.1002/hlca.201300256

Reference yield:

: 631416-68-7
(3S)-3-((4-methoxyphenyl)methyl)oxy-5-formyl-1-pentene

: 1242065-84-4
(1R)-1,2-anhydro-3,5-dideoxy-1-ethenyl-4-O-{(3S)-3-[ (4-methoxybenzyl)oxy]pent-4-enoyl}-D-threopentitol

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / tert-butyl alcohol; water / 6 h / 25 °C / Inert atmosphere

2.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

2.2: 10 h / Inert atmosphere

With dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; dicyclohexyl-carbodiimide; In dichloromethane; water; tert-butyl alcohol; 2.1: |Steglich Esterification / 2.2: |Steglich Esterification;
DOI:10.1002/hlca.201300256