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

Base Information

• Chemical Name: methyl {(1S)-1-[(4'R,5'R)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]-2-hydroxyethyl}carbamate
• CAS No.: 1611460-06-0
• Molecular Formula: C₁₇H₂₅NO₆
• Molecular Weight: 339.389

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 15 articles about methyl {(1S)-1-[(4'R,5'R)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]-2-hydroxyethyl}carbamate 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:

C18H18O5 (1611459-82-5) → methyl {(1S)-1-[(4'R,5'R)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]-2-hydroxyethyl}carbamate (1611460-06-0)

Guidance literature:

Multi-step reaction with 12 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: triethylamine / dichloromethane / 0.67 h / 0 - 20 °C / Inert atmosphere

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

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

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

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

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

12.2: 0.01 h / -78 - 0 °C / Inert atmosphere

With methanol; sodium tetrahydroborate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; ozone; triethylamine; mesitylenecarbonitrile oxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; ethanol; n-heptane; dichloromethane; toluene; acetonitrile; mineral oil; 5.1: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1016/j.tetasy.2014.04.002

Reference yield:

C14H18O4 (866772-34-1) → methyl {(1S)-1-[(4'R,5'R)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]-2-hydroxyethyl}carbamate (1611460-06-0)

Guidance literature:

Multi-step reaction with 8 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

With sodium hydride; diisobutylaluminium hydride; ozone; triethylamine; mesitylenecarbonitrile oxide; In tetrahydrofuran; methanol; ethanol; n-heptane; dichloromethane; toluene; acetonitrile; mineral oil; 1.1: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1016/j.tetasy.2014.04.002

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose (34370-91-7,59358-33-7,68354-70-1,70798-12-8,19139-80-1) → methyl {(1S)-1-[(4'R,5'R)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]-2-hydroxyethyl}carbamate (1611460-06-0)

Guidance literature:

Multi-step reaction with 15 steps

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

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

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

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

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

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

7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 1 h / Inert atmosphere; Reflux

8.1: dichloromethane / 20 °C

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

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

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

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

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

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

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

15.2: 0.01 h / -78 - 0 °C / Inert atmosphere

With pyridine; methanol; dmap; sodium tetrahydroborate; sodium periodate; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; ozone; triethylamine; mesitylenecarbonitrile oxide; trifluoroacetic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In methanol; ethanol; n-heptane; dichloromethane; water; toluene; acetonitrile; 8.1: |Wittig Olefination;

DOI:10.1016/j.tetasy.2014.04.002

upstream raw materials:

C₁₈H₁₈O₅

C₁₄H₁₈O₄

C₁₇H₂₄O₆S

C₁₈H₂₅NO₄S

Downstream raw materials:

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

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

(4R)-4-[(1'R,2'R)-2'-(benzyloxy)-1',3'-dihydroxypropyl]oxazolidin-2-one

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

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