(4R)-3-benzyl-4-[(1'R,2'R)-1',2'-bis(benzyloxy)-3'-(trityloxy)propyl]oxazolidin-2-one

Base Information

Chemical Name:(4R)-3-benzyl-4-[(1'R,2'R)-1',2'-bis(benzyloxy)-3'-(trityloxy)propyl]oxazolidin-2-one
CAS No.:1611460-15-1
Molecular Formula:C₄₆H₄₃NO₅
Molecular Weight:689.851
Hs Code.:

Synonyms:(4R)-3-benzyl-4-[(1'R,2'R)-1',2'-bis(benzyloxy)-3'-(trityloxy)propyl]oxazolidin-2-one

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Chemical Property of (4R)-3-benzyl-4-[(1'R,2'R)-1',2'-bis(benzyloxy)-3'-(trityloxy)propyl]oxazolidin-2-one

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Technology Process of (4R)-3-benzyl-4-[(1'R,2'R)-1',2'-bis(benzyloxy)-3'-(trityloxy)propyl]oxazolidin-2-one

There total 26 articles about (4R)-3-benzyl-4-[(1'R,2'R)-1',2'-bis(benzyloxy)-3'-(trityloxy)propyl]oxazolidin-2-one 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%

: 1611460-13-9
(4R)-4-[(1'R,2'R)-2'-(benzyloxy)-1'-hydroxy-3'-(trityloxy)propyl]oxazolidin-2-one

: 100-39-0
benzyl bromide

: 1611460-15-1
(4R)-3-benzyl-4-[(1'R,2'R)-1',2'-bis(benzyloxy)-3'-(trityloxy)propyl]oxazolidin-2-one

Guidance literature:: (4R)-4-[(1'R,2'R)-2'-(benzyloxy)-1'-hydroxy-3'-(trityloxy)propyl]oxazolidin-2-one; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; Inert atmosphere;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 0.5h; Inert atmosphere;
DOI:10.1016/j.tetasy.2014.04.002

Reference yield:

: 866772-34-1
C₁₄H₁₈O₄

: 1611460-15-1
(4R)-3-benzyl-4-[(1'R,2'R)-1',2'-bis(benzyloxy)-3'-(trityloxy)propyl]oxazolidin-2-one

Guidance literature:: Multi-step reaction with 12 steps

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

1.2: 1.5 h / 0 °C / Inert atmosphere

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

3.1: triethylamine / dichloromethane / 0.67 h / 0 - 20 °C / Inert atmosphere

4.1: acetonitrile / 6.25 h / 0 - 20 °C / Inert atmosphere

5.1: n-heptane / 2 h / 90 °C / Inert atmosphere

6.1: methanol / 14 h / 0 - 20 °C / Inert atmosphere

7.1: mesitylenecarbonitrile oxide / acetonitrile / 1.5 h / 20 °C / Inert atmosphere

8.1: ozone / ethanol / 0.25 h / -78 °C

8.2: 0.01 h / -78 - 0 °C / Inert atmosphere

9.1: sodium hydride / mineral oil; tetrahydrofuran / 0.33 h / 0 - 20 °C / Inert atmosphere

10.1: toluene-4-sulfonic acid / methanol / 1.5 h / 20 °C / Inert atmosphere

11.1: dmap; pyridine / 22 h / 60 °C / Inert atmosphere

12.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 °C / Inert atmosphere

12.2: 0.5 h / 0 - 20 °C / Inert atmosphere

With pyridine; dmap; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; triethylamine; mesitylenecarbonitrile oxide; In tetrahydrofuran; methanol; ethanol; n-heptane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; 1.1: |Horner-Wadsworth-Emmons Olefination;
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

: 1611460-15-1
(4R)-3-benzyl-4-[(1'R,2'R)-1',2'-bis(benzyloxy)-3'-(trityloxy)propyl]oxazolidin-2-one

Guidance literature:: Multi-step reaction with 16 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

14.1: toluene-4-sulfonic acid / methanol / 1.5 h / 20 °C / Inert atmosphere

15.1: dmap; pyridine / 22 h / 60 °C / Inert atmosphere

16.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 °C / Inert atmosphere

16.2: 0.5 h / 0 - 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; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; 9.1: |Horner-Wadsworth-Emmons Olefination / 12.1: |Overman Rearrangement;
DOI:10.1016/j.tetasy.2014.04.002