(3R,6S,7R)-3-(benzyloxy)-7-((4-methoxybenzyl)oxy)-6-(methoxymethoxy)dodecan-1-ol

Base Information

• Chemical Name: (3R,6S,7R)-3-(benzyloxy)-7-((4-methoxybenzyl)oxy)-6-(methoxymethoxy)dodecan-1-ol
• CAS No.: 1609652-02-9
• Molecular Formula: C₂₉H₄₄O₆
• Molecular Weight: 488.665
• Mol file: 1609652-02-9.mol

Synonyms:(3R,6S,7R)-3-(benzyloxy)-7-((4-methoxybenzyl)oxy)-6-(methoxymethoxy)dodecan-1-ol

Chemical Property of (3R,6S,7R)-3-(benzyloxy)-7-((4-methoxybenzyl)oxy)-6-(methoxymethoxy)dodecan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,6S,7R)-3-(benzyloxy)-7-((4-methoxybenzyl)oxy)-6-(methoxymethoxy)dodecan-1-ol

There total 14 articles about (3R,6S,7R)-3-(benzyloxy)-7-((4-methoxybenzyl)oxy)-6-(methoxymethoxy)dodecan-1-ol 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: 86.0%

(4R)-4-((3S,4R)-4-((4-methoxybenzyl)oxy)-3-(methoxymethoxy)nonyl)-2-phenyl-1,3-dioxane (1609652-01-8) → (3R,6S,7R)-3-(benzyloxy)-7-((4-methoxybenzyl)oxy)-6-(methoxymethoxy)dodecan-1-ol (1609652-02-9)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at -20 ℃; for 2h; regioselective reaction;

DOI:10.1039/c4ob00323c

Reference yield:

C18H28O5S (1609651-94-6) → (3R,6S,7R)-3-(benzyloxy)-7-((4-methoxybenzyl)oxy)-6-(methoxymethoxy)dodecan-1-ol (1609652-02-9)

Guidance literature:

Multi-step reaction with 12 steps

1.1: toluene-4-sulfonic acid / methanol / 0 - 20 °C

2.1: potassium carbonate / methanol / 2 h / 0 °C

3.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C

3.2: 0 - 20 °C

4.1: copper(I) bromide / tetrahydrofuran; diethyl ether / 0 °C

5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 8 h / 0 - 20 °C

6.1: ozone / dichloromethane / -78 °C / Inert atmosphere

7.1: benzene / 2 h / 20 °C

8.1: diisobutylaluminium hydride / dichloromethane; toluene / 20 °C / Cooling

9.1: titanium(IV) isopropylate; D-(-)-diisopropyl tartrate / dichloromethane / 0.5 h / -20 °C / Molecular sieve

9.2: 3 h / -20 °C

10.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 2.5 h / 0 °C

11.1: pyridinium p-toluenesulfonate / dichloromethane / 0 °C

12.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -20 °C

With titanium(IV) isopropylate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; ozone; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; copper(I) bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; mineral oil; benzene; 7.1: |Wittig Olefination / 9.1: |Sharpless Asymmetric Epoxidation;

DOI:10.1039/c4ob00323c

Reference yield:

C11H20O3 (1609651-93-5) → (3R,6S,7R)-3-(benzyloxy)-7-((4-methoxybenzyl)oxy)-6-(methoxymethoxy)dodecan-1-ol (1609652-02-9)

Guidance literature:

Multi-step reaction with 14 steps

1.1: palladium 10% on activated carbon; hydrogen / ethanol

2.1: dmap; triethylamine / dichloromethane / 0 - 20 °C

3.1: toluene-4-sulfonic acid / methanol / 0 - 20 °C

4.1: potassium carbonate / methanol / 2 h / 0 °C

5.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C

5.2: 0 - 20 °C

6.1: copper(I) bromide / tetrahydrofuran; diethyl ether / 0 °C

7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 8 h / 0 - 20 °C

8.1: ozone / dichloromethane / -78 °C / Inert atmosphere

9.1: benzene / 2 h / 20 °C

10.1: diisobutylaluminium hydride / dichloromethane; toluene / 20 °C / Cooling

11.1: titanium(IV) isopropylate; D-(-)-diisopropyl tartrate / dichloromethane / 0.5 h / -20 °C / Molecular sieve

11.2: 3 h / -20 °C

12.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 2.5 h / 0 °C

13.1: pyridinium p-toluenesulfonate / dichloromethane / 0 °C

14.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -20 °C

With titanium(IV) isopropylate; dmap; palladium 10% on activated carbon; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; copper(I) bromide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; toluene; mineral oil; benzene; 9.1: |Wittig Olefination / 11.1: |Sharpless Asymmetric Epoxidation;

DOI:10.1039/c4ob00323c

upstream raw materials:

(3R,6S,7R)-7-((4-methoxybenzyl)oxy)-6-(methoxymethoxy)dodecane-1,3-diol

(4R)-4-((3S,4R)-4-((4-methoxybenzyl)oxy)-3-(methoxymethoxy)nonyl)-2-phenyl-1,3-dioxane

C₁₁H₂₀O₃

((4S,5R)-2,2-dimethyl-5-propyl-1,3-dioxolan-4-yl)methanol

Downstream raw materials:

(S)-4-benzyl-3-((2S,3R,5R,8S,9R)-5-(benzyloxy)-3-hydroxy-9-((4-methoxybenzyl)oxy)-8-(methoxymethoxy)-2-methyltetradecanoyl)oxazolidin-2-one

(S)-4-benzyl-3-((2S,3R,8S,9R,E)-3-hydroxy-9-((4-methoxybenzyl)oxy)-8-(methoxymethoxy)-2-methyltetradec-4-enoyl)oxazolidin-2-one

(S)-4-benzyl-3-((2S,3R,5R,8S,9R)-5-(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)-9-((4-methoxybenzyl)oxy)-8-(methoxymethoxy)-2-methyltetradecanoyl)oxazolidin-2-one

C₃₀H₅₄O₇Si