(4R,5R)-5-(benzyloxy)-4-[(1'S)-1'-isothiocyanatoallyl]-2,2-dimethyl-1,3-dioxane

Base Information

• Chemical Name: (4R,5R)-5-(benzyloxy)-4-[(1'S)-1'-isothiocyanatoallyl]-2,2-dimethyl-1,3-dioxane
• CAS No.: 1611459-93-8
• Molecular Formula: C₁₇H₂₁NO₃S
• Molecular Weight: 319.425
• Mol file: 1611459-93-8.mol

Synonyms:(4R,5R)-5-(benzyloxy)-4-[(1'S)-1'-isothiocyanatoallyl]-2,2-dimethyl-1,3-dioxane

Chemical Property of (4R,5R)-5-(benzyloxy)-4-[(1'S)-1'-isothiocyanatoallyl]-2,2-dimethyl-1,3-dioxane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5R)-5-(benzyloxy)-4-[(1'S)-1'-isothiocyanatoallyl]-2,2-dimethyl-1,3-dioxane

There total 25 articles about (4R,5R)-5-(benzyloxy)-4-[(1'S)-1'-isothiocyanatoallyl]-2,2-dimethyl-1,3-dioxane 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:

(4R,5R)-5-(benzyloxy)-2,2-dimethyl-4-[(E)-3'-thiocyanatoprop-1'-en-1'-yl]-1,3-dioxane (1611459-88-1) → (4R,5R)-5-(benzyloxy)-4-[(1'R)-1'-isothiocyanatoallyl]-2,2-dimethyl-1,3-dioxane (1611459-91-6) + (4R,5R)-5-(benzyloxy)-4-[(1'S)-1'-isothiocyanatoallyl]-2,2-dimethyl-1,3-dioxane (1611459-93-8)

Guidance literature:

In n-heptane; at 90 ℃; for 2h; Temperature; Overall yield = 96 %; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tetasy.2014.04.002

Reference yield:

C18H18O5 (1611459-82-5) → (4R,5R)-5-(benzyloxy)-4-[(1'S)-1'-isothiocyanatoallyl]-2,2-dimethyl-1,3-dioxane (1611459-93-8)

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: 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

With methanol; sodium tetrahydroborate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; 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) → (4R,5R)-5-(benzyloxy)-4-[(1'S)-1'-isothiocyanatoallyl]-2,2-dimethyl-1,3-dioxane (1611459-93-8)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1016/j.tetasy.2014.04.002

upstream raw materials:

C₁₈H₁₈O₅

C₁₄H₁₈O₄

C₁₇H₂₄O₆S

3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

Downstream raw materials:

C₁₈H₂₅NO₄S

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

(4S)-3-benzyl-4-[(1'R,2'R,3'E)-1',2'-bis(benzyloxy)hexadec-3'-en-1'-yl]oxazolidin-2-one

(4S)-3-benzyl-4-[(1'R,2'R,3'Z)-1',2'-bis(benzyloxy)hexadec-3'-en-1'-yl]oxazolidin-2-one