N-{(1'R)-1'-[(4R,5R)-5-(benzyloxy)-2,2-dimethyl-1,3-dioxan-4-yl]-2'-hydroxyethyl}-2,2,2-trichloroacetamide

Base Information

Chemical Name:N-{(1'R)-1'-[(4R,5R)-5-(benzyloxy)-2,2-dimethyl-1,3-dioxan-4-yl]-2'-hydroxyethyl}-2,2,2-trichloroacetamide
CAS No.:1611460-09-3
Molecular Formula:C₁₇H₂₂Cl₃NO₅
Molecular Weight:426.724
Hs Code.:

Synonyms:N-{(1'R)-1'-[(4R,5R)-5-(benzyloxy)-2,2-dimethyl-1,3-dioxan-4-yl]-2'-hydroxyethyl}-2,2,2-trichloroacetamide

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Chemical Property of N-{(1'R)-1'-[(4R,5R)-5-(benzyloxy)-2,2-dimethyl-1,3-dioxan-4-yl]-2'-hydroxyethyl}-2,2,2-trichloroacetamide

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Technology Process of N-{(1'R)-1'-[(4R,5R)-5-(benzyloxy)-2,2-dimethyl-1,3-dioxan-4-yl]-2'-hydroxyethyl}-2,2,2-trichloroacetamide

There total 16 articles about N-{(1'R)-1'-[(4R,5R)-5-(benzyloxy)-2,2-dimethyl-1,3-dioxan-4-yl]-2'-hydroxyethyl}-2,2,2-trichloroacetamide 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: 63.0%

: 1611459-97-2
N-{(1'R)-1-[(4''R,5''R)-5''-(benzyloxy)-2'',2''-dimethyl-1'',3''-dioxan-4''-yl]allyl}-2,2,2-trichloroacetamide

: 1611460-07-1
(4R)-4-[(4'R,5'R)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]oxazolidin-2-one

: 1611460-09-3
N-{(1'R)-1'-[(4R,5R)-5-(benzyloxy)-2,2-dimethyl-1,3-dioxan-4-yl]-2'-hydroxyethyl}-2,2,2-trichloroacetamide

Guidance literature:: N-{(1'R)-1-[(4''R,5''R)-5''-(benzyloxy)-2'',2''-dimethyl-1'',3''-dioxan-4''-yl]allyl}-2,2,2-trichloroacetamide; With ozone; In methanol; dichloromethane; at -78 ℃; for 0.25h;

With sodium tetrahydroborate; In methanol; dichloromethane; at -78 - 20 ℃; for 0.1h; Inert atmosphere;
DOI:10.1016/j.tetasy.2014.04.002

Reference yield:

: 185541-37-1
1,2-O-isopropylidene-3-O-benzyl-5-O-triphenylmethyl-α-D-xylofuranoside

: 1611460-09-3
N-{(1'R)-1'-[(4R,5R)-5-(benzyloxy)-2,2-dimethyl-1,3-dioxan-4-yl]-2'-hydroxyethyl}-2,2,2-trichloroacetamide

Guidance literature:: Multi-step reaction with 13 steps

1.1: toluene-4-sulfonic acid / methanol; dichloromethane / 1 h / 20 °C / Inert atmosphere

2.1: dmap; pyridine / 1.67 h / 0 - 20 °C / Inert atmosphere

3.1: trifluoroacetic acid / water / 6 h / 0 °C / Inert atmosphere

4.1: sodium periodate / methanol; water / 1 h / 20 °C / Inert atmosphere

5.1: sodium tetrahydroborate / methanol; dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

6.1: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere

7.1: potassium carbonate; methanol / 4.42 h / 0 - 20 °C / Inert atmosphere

8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 1 h / Inert atmosphere; Reflux

9.1: sodium hydride / mineral oil; tetrahydrofuran / 0.42 h / -10 - 0 °C / Inert atmosphere

9.2: 1.5 h / 0 °C / Inert atmosphere

10.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -50 - -30 °C / Inert atmosphere

11.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

11.2: 0.5 h / 0 °C / Inert atmosphere

12.1: potassium carbonate / o-xylene / 1.5 h / 150 °C / Sealed tube; Inert atmosphere; Microwave irradiation

13.1: ozone / methanol; dichloromethane / 0.25 h / -78 °C

13.2: 0.1 h / -78 - 20 °C / Inert atmosphere

With pyridine; methanol; dmap; sodium tetrahydroborate; sodium periodate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; ozone; trifluoroacetic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; dichloromethane; o-xylene; water; toluene; acetonitrile; mineral oil; 9.1: |Horner-Wadsworth-Emmons Olefination / 12.1: |Overman Rearrangement;
DOI:10.1016/j.tetasy.2014.04.002

Reference yield:

: 1611459-82-5
C₁₈H₁₈O₅

: 1611460-09-3
N-{(1'R)-1'-[(4R,5R)-5-(benzyloxy)-2,2-dimethyl-1,3-dioxan-4-yl]-2'-hydroxyethyl}-2,2,2-trichloroacetamide

Guidance literature:: Multi-step reaction with 9 steps

1.1: sodium tetrahydroborate / methanol; dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere

3.1: potassium carbonate; methanol / 4.42 h / 0 - 20 °C / Inert atmosphere

4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 1 h / Inert atmosphere; Reflux

5.1: sodium hydride / mineral oil; tetrahydrofuran / 0.42 h / -10 - 0 °C / Inert atmosphere

5.2: 1.5 h / 0 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -50 - -30 °C / Inert atmosphere

7.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

7.2: 0.5 h / 0 °C / Inert atmosphere

8.1: potassium carbonate / o-xylene / 1.5 h / 150 °C / Sealed tube; Inert atmosphere; Microwave irradiation

9.1: ozone / methanol; dichloromethane / 0.25 h / -78 °C

9.2: 0.1 h / -78 - 20 °C / Inert atmosphere

With methanol; sodium tetrahydroborate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; ozone; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; dichloromethane; o-xylene; toluene; acetonitrile; mineral oil; 5.1: |Horner-Wadsworth-Emmons Olefination / 8.1: |Overman Rearrangement;
DOI:10.1016/j.tetasy.2014.04.002