(4aR,6R,8aR)-6-((tert-butyldimethylsilyl)oxy)-4-(((4-methoxybenzyl)oxy)methyl)-7-methyl-4a,5,6,8a-tetrahydro-2H-chromen-2-one

Base Information

• Chemical Name: (4aR,6R,8aR)-6-((tert-butyldimethylsilyl)oxy)-4-(((4-methoxybenzyl)oxy)methyl)-7-methyl-4a,5,6,8a-tetrahydro-2H-chromen-2-one
• CAS No.: 1376709-03-3
• Molecular Formula: C₂₅H₃₆O₅Si
• Molecular Weight: 444.643
• Mol file: 1376709-03-3.mol

Synonyms:(4aR,6R,8aR)-6-((tert-butyldimethylsilyl)oxy)-4-(((4-methoxybenzyl)oxy)methyl)-7-methyl-4a,5,6,8a-tetrahydro-2H-chromen-2-one

Chemical Property of (4aR,6R,8aR)-6-((tert-butyldimethylsilyl)oxy)-4-(((4-methoxybenzyl)oxy)methyl)-7-methyl-4a,5,6,8a-tetrahydro-2H-chromen-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,6R,8aR)-6-((tert-butyldimethylsilyl)oxy)-4-(((4-methoxybenzyl)oxy)methyl)-7-methyl-4a,5,6,8a-tetrahydro-2H-chromen-2-one

There total 11 articles about (4aR,6R,8aR)-6-((tert-butyldimethylsilyl)oxy)-4-(((4-methoxybenzyl)oxy)methyl)-7-methyl-4a,5,6,8a-tetrahydro-2H-chromen-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: 93.0%

(4aR,6R,8aR)-6-((tert-butyldimethylsilyl)oxy)-4-(hydroxymethyl)-7-methyl-4a,5,6,8a-tetrahydro-2H-chromen-2-one (1376709-30-6) + O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → (4aR,6R,8aR)-6-((tert-butyldimethylsilyl)oxy)-4-(((4-methoxybenzyl)oxy)methyl)-7-methyl-4a,5,6,8a-tetrahydro-2H-chromen-2-one (1376709-03-3)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1021/ja303529z

Reference yield:

(4S,5R)-5-(3-chloroprop-1-en-2-yl)-4-hydroxy-2-methylcyclohex-2-enone (1376709-08-8) → (4aR,6R,8aR)-6-((tert-butyldimethylsilyl)oxy)-4-(((4-methoxybenzyl)oxy)methyl)-7-methyl-4a,5,6,8a-tetrahydro-2H-chromen-2-one (1376709-03-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 3 h / 0 - 20 °C / Inert atmosphere

2.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0.17 h / -78 - 20 °C / Inert atmosphere

3.1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 20 °C

4.1: sodium iodide / acetone / 20 °C

5.1: samarium diiodide / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 - 40 °C

7.1: mercury(II) diacetate / toluene / 2 h / 80 °C / Inert atmosphere

7.2: 0.5 h / 20 °C / Inert atmosphere

7.3: 0.5 h / Inert atmosphere

8.1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere

9.1: methanol; water / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

10.1: toluene-4-sulfonic acid / dichloromethane / 5 h / 20 °C

With 1H-imidazole; methanol; sodium tetrahydroborate; samarium diiodide; cerium(III) chloride heptahydrate; mercury(II) diacetate; water; sodium hydrogencarbonate; toluene-4-sulfonic acid; triphenylphosphine; sodium iodide; diethylazodicarboxylate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; 1.1: Mitsunobu reaction / 2.1: Luche reduction / 4.1: Finkelstein reaction / 5.1: Barbier reaction;

DOI:10.1021/ja303529z

Reference yield:

(1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-6-(3-chloroprop-1-en-2-yl)-3-methylcyclohex-2-en-1-yl formate (1376709-28-2) → (4aR,6R,8aR)-6-((tert-butyldimethylsilyl)oxy)-4-(((4-methoxybenzyl)oxy)methyl)-7-methyl-4a,5,6,8a-tetrahydro-2H-chromen-2-one (1376709-03-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium iodide / acetone / 20 °C

2.1: samarium diiodide / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 - 40 °C

4.1: mercury(II) diacetate / toluene / 2 h / 80 °C / Inert atmosphere

4.2: 0.5 h / 20 °C / Inert atmosphere

4.3: 0.5 h / Inert atmosphere

5.1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere

6.1: methanol; water / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

7.1: toluene-4-sulfonic acid / dichloromethane / 5 h / 20 °C

With methanol; samarium diiodide; mercury(II) diacetate; water; sodium hydrogencarbonate; toluene-4-sulfonic acid; sodium iodide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; 1.1: Finkelstein reaction / 2.1: Barbier reaction;

DOI:10.1021/ja303529z

upstream raw materials:

(1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-6-(3-chloroprop-1-en-2-yl)-3-methylcyclohex-2-en-1-yl formate

(1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-6-(3-iodoprop-1-en-2-yl)-3-methylcyclohex-2-en-1-yl formate

(4S,5R)-5-(3-chloroprop-1-en-2-yl)-4-hydroxy-2-methylcyclohex-2-enone

(4aR,6R,8aR)-6-((tert-butyldimethylsilyl)oxy)-4-(hydroxymethyl)-7-methyl-4a,5,6,8a-tetrahydro-2H-chromen-2-one

Downstream raw materials:

C₃₃H₄₄O₅