[(2R,4S,5S)-5-((S)-6-Benzyloxy-5-methyl-hexyl)-4-methyl-tetrahydro-furan-2-yl]-methanol

Base Information

• Chemical Name: [(2R,4S,5S)-5-((S)-6-Benzyloxy-5-methyl-hexyl)-4-methyl-tetrahydro-furan-2-yl]-methanol
• CAS No.: 900159-37-7
• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.472
• Mol file: 900159-37-7.mol

Synonyms:[(2R,4S,5S)-5-((S)-6-Benzyloxy-5-methyl-hexyl)-4-methyl-tetrahydro-furan-2-yl]-methanol

Chemical Property of [(2R,4S,5S)-5-((S)-6-Benzyloxy-5-methyl-hexyl)-4-methyl-tetrahydro-furan-2-yl]-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,4S,5S)-5-((S)-6-Benzyloxy-5-methyl-hexyl)-4-methyl-tetrahydro-furan-2-yl]-methanol

There total 20 articles about [(2R,4S,5S)-5-((S)-6-Benzyloxy-5-methyl-hexyl)-4-methyl-tetrahydro-furan-2-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: 95.0%

(2S,3S,5R)-2-((S)-6-Benzyloxy-5-methyl-hexyl)-3-methyl-5-trityloxymethyl-tetrahydro-furan (900159-36-6) → [(2R,4S,5S)-5-((S)-6-Benzyloxy-5-methyl-hexyl)-4-methyl-tetrahydro-furan-2-yl]-methanol (900159-37-7)

Guidance literature:

With acetic acid; at 50 - 55 ℃; for 3h;

DOI:10.1021/jo0605086

Reference yield:

Acetic acid (1R,3S)-3-methyl-4-oxo-1-trityloxymethyl-butyl ester (900159-30-0) → [(2R,4S,5S)-5-((S)-6-Benzyloxy-5-methyl-hexyl)-4-methyl-tetrahydro-furan-2-yl]-methanol (900159-37-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: (R,R)-1,2-diamino-1,2-diphenylethane-bis(toluenesulfonamide); boron tribromide / CH₂Cl₂ / 6 h / 20 °C

1.2: 85 percent / CH₂Cl₂ / 2 h / -78 °C

2.1: 99 percent / pyridine / 48 h / 20 °C

3.1: 99 percent / KOH / bis-(2-methoxy-ethyl) ether; ethane-1,2-diol / 1.5 h / 40 °C

4.1: borane-dimethyl sulfide / tetrahydrofuran / 0 - 20 °C

4.2: 83 percent / aq. NaOH; aq. H₂O₂; ethanol / tetrahydrofuran / 2 h / 20 °C

5.1: 95 percent / PPh₃; imidazole; I₂ / tetrahydrofuran / 0 - 20 °C

6.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - -30 °C

6.2: 4.89 g / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h

7.1: 3.26 g / sodium amalgam / ethanol / 0 - 20 °C

8.1: 95 percent / aq. HOAc / 3 h / 50 - 55 °C

With 1H-imidazole; potassium hydroxide; sodium amalgam; n-butyllithium; dimethylsulfide borane complex; (R,R)-1,2-diamino-1,2-diphenylethane-bis(toluenesulfonamide); iodine; boron tribromide; acetic acid; triphenylphosphine; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; diethylene glycol dimethyl ether; ethylene glycol;

DOI:10.1021/jo0605086

Reference yield:

Acetic acid (1R,3S)-4-hydroxy-3-methyl-1-trityloxymethyl-butyl ester (900159-29-7) → [(2R,4S,5S)-5-((S)-6-Benzyloxy-5-methyl-hexyl)-4-methyl-tetrahydro-furan-2-yl]-methanol (900159-37-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

2.1: (R,R)-1,2-diamino-1,2-diphenylethane-bis(toluenesulfonamide); boron tribromide / CH₂Cl₂ / 6 h / 20 °C

2.2: 85 percent / CH₂Cl₂ / 2 h / -78 °C

3.1: 99 percent / pyridine / 48 h / 20 °C

4.1: 99 percent / KOH / bis-(2-methoxy-ethyl) ether; ethane-1,2-diol / 1.5 h / 40 °C

5.1: borane-dimethyl sulfide / tetrahydrofuran / 0 - 20 °C

5.2: 83 percent / aq. NaOH; aq. H₂O₂; ethanol / tetrahydrofuran / 2 h / 20 °C

6.1: 95 percent / PPh₃; imidazole; I₂ / tetrahydrofuran / 0 - 20 °C

7.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - -30 °C

7.2: 4.89 g / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h

8.1: 3.26 g / sodium amalgam / ethanol / 0 - 20 °C

9.1: 95 percent / aq. HOAc / 3 h / 50 - 55 °C

With 1H-imidazole; potassium hydroxide; sodium amalgam; n-butyllithium; dimethylsulfide borane complex; (R,R)-1,2-diamino-1,2-diphenylethane-bis(toluenesulfonamide); iodine; boron tribromide; Dess-Martin periodane; acetic acid; triphenylphosphine; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; diethylene glycol dimethyl ether; ethylene glycol;

DOI:10.1021/jo0605086

upstream raw materials:

(2S,3S,5R)-2-((S)-6-Benzyloxy-5-methyl-hexyl)-3-methyl-5-trityloxymethyl-tetrahydro-furan

Acetic acid (1R,3S)-3-methyl-4-oxo-1-trityloxymethyl-butyl ester

(2S,3S,5R)-2-Allyl-3-methyl-5-trityloxymethyl-tetrahydro-furan

Acetic acid (1R,3S)-4-hydroxy-3-methyl-1-trityloxymethyl-butyl ester

Downstream raw materials:

Acetic acid (R)-2-[(2R,4S,5S)-5-((S)-6-benzyloxy-5-methyl-hexyl)-4-methyl-tetrahydro-furan-2-yl]-1-{2-[(1R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-1-methyl-3-methylene-octyl]-[1,3]dithian-2-yl}-ethyl ester

(R)-2-[(2R,4S,5S)-5-((S)-6-Benzyloxy-5-methyl-hexyl)-4-methyl-tetrahydro-furan-2-yl]-1-{2-[(1R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-1-methyl-3-methylene-octyl]-[1,3]dithian-2-yl}-ethanol

(2S,3S,5R)-2-((S)-6-Benzyloxy-5-methyl-hexyl)-5-[1,3]dithian-2-ylmethyl-3-methyl-tetrahydro-furan

[(2R,4S,5S)-5-((S)-6-Benzyloxy-5-methyl-hexyl)-4-methyl-tetrahydro-furan-2-yl]-acetaldehyde