[(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol

Base Information

• Chemical Name: [(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol
• CAS No.: 1358580-72-9
• Molecular Formula: C₄₃H₄₁ClO₇
• Molecular Weight: 705.247
• Mol file: 1358580-72-9.mol

Synonyms:[(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol

Chemical Property of [(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol

There total 13 articles about [(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol 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: 50.4%

[(3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-yl]methanol (1358580-71-8) → [(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol (1358580-72-9)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 1.5h;

Reference yield:

2.3-dihydrobenzofuran (496-16-2) → [(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol (1358580-72-9)

Guidance literature:

Multi-step reaction with 11 steps

1.1: aluminum (III) chloride / dichloromethane / 2 h

2.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 0.5 h / 0 °C

3.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 16 h

4.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 1 h / -78 °C

4.2: 3 h / -78 °C

4.3: 16 h

5.1: pyridine; dmap / 16 h

6.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 20 °C

6.2: 16 h

7.1: acetyl chloride; methanol / 1 h

8.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 2.66 h / 2 °C

9.1: sodium hydroxide; water / 1,4-dioxane / 16 h / 70 °C

10.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 0.5 h

11.1: trifluoroacetic acid / dichloromethane / 1.5 h

With pyridine; methanol; triethylsilane; dmap; aluminum (III) chloride; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; water; sodium hydride; acetyl chloride; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; mineral oil;

Reference yield:

(5-bromo-2-chloro-phenyl)-(2,3-dihydrobenzofuran-5-yl)methanone (1096875-61-4) → [(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol (1358580-72-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 0.5 h / 0 °C

2.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 16 h

3.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 1 h / -78 °C

3.2: 3 h / -78 °C

3.3: 16 h

4.1: pyridine; dmap / 16 h

5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 20 °C

5.2: 16 h

6.1: acetyl chloride; methanol / 1 h

7.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 2.66 h / 2 °C

8.1: sodium hydroxide; water / 1,4-dioxane / 16 h / 70 °C

9.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 0.5 h

10.1: trifluoroacetic acid / dichloromethane / 1.5 h

With pyridine; methanol; triethylsilane; dmap; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; water; sodium hydride; acetyl chloride; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; mineral oil;

upstream raw materials:

2.3-dihydrobenzofuran

(5-bromo-2-chloro-phenyl)-(2,3-dihydrobenzofuran-5-yl)methanone

(5-bromo-2-chloro-phenyl)-(2,3-dihydrobenzofuran-5-yl)methanol

5-[(5-bromo-2-chloro-phenyl)methyl]-2,3-dihydrobenzofuran