(6S)-1,4-di-O-benzyl-6-benzylamino-6-C-n-butyl-6-deoxy-2,3-O-isopropylidene-α-L-sorbofuranose

Base Information

• Chemical Name: (6S)-1,4-di-O-benzyl-6-benzylamino-6-C-n-butyl-6-deoxy-2,3-O-isopropylidene-α-L-sorbofuranose
• CAS No.: 473931-79-2
• Molecular Formula: C₃₄H₄₃NO₅
• Molecular Weight: 545.719
• Mol file: 473931-79-2.mol

Synonyms:(6S)-1,4-di-O-benzyl-6-benzylamino-6-C-n-butyl-6-deoxy-2,3-O-isopropylidene-α-L-sorbofuranose

Chemical Property of (6S)-1,4-di-O-benzyl-6-benzylamino-6-C-n-butyl-6-deoxy-2,3-O-isopropylidene-α-L-sorbofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6S)-1,4-di-O-benzyl-6-benzylamino-6-C-n-butyl-6-deoxy-2,3-O-isopropylidene-α-L-sorbofuranose

There total 9 articles about (6S)-1,4-di-O-benzyl-6-benzylamino-6-C-n-butyl-6-deoxy-2,3-O-isopropylidene-α-L-sorbofuranose 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: 69.0%

n-butyllithium (109-72-8,29786-93-4) + 3,6-di-O-benzyl-4,5-O-isopropylidene-D-xylo-aldehydohexos-5-ulo-2,5-furanose N-benzylimine (302788-34-7) → (6S)-1,4-di-O-benzyl-6-benzylamino-6-C-n-butyl-6-deoxy-2,3-O-isopropylidene-α-L-sorbofuranose (473931-79-2)

Guidance literature:

With boron trifluoride diethyl etherate; In diethyl ether; at -78 - 0 ℃;

DOI:10.1021/jo0203903

Reference yield:

benzyl bromide (100-39-0) → (6S)-1,4-di-O-benzyl-6-benzylamino-6-C-n-butyl-6-deoxy-2,3-O-isopropylidene-α-L-sorbofuranose (473931-79-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

1.2: 98 percent / tetrabutylammonium bromide / tetrahydrofuran / 3 h / 20 °C

2.1: 99 percent / H₂SO₄ / acetone; H₂O / 3 h / 20 °C

3.1: 95 percent / pyridine / 24 h / 50 °C

4.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

4.2: 99 percent / tetrabutylammonium bromide / tetrahydrofuran / 4 h / 20 °C

5.1: 96 percent / HBr / acetic acid / 10 - 15 °C

6.1: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

7.1: 100 percent / molecular sieves 4 Angstroem / CH₂Cl₂ / 3 h / 4 °C

8.1: 69 percent / BF₃*Et₂O / diethyl ether / -78 - 0 °C

With pyridine; 4 A molecular sieve; sulfuric acid; boron trifluoride diethyl etherate; hydrogen bromide; sodium hydride; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetic acid; acetone;

DOI:10.1021/jo0203903

Reference yield:

2,3:4,6-bis-O-isopropylidene-L-sorbose (17682-70-1) → (6S)-1,4-di-O-benzyl-6-benzylamino-6-C-n-butyl-6-deoxy-2,3-O-isopropylidene-α-L-sorbofuranose (473931-79-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

1.2: 98 percent / tetrabutylammonium bromide / tetrahydrofuran / 3 h / 20 °C

2.1: 99 percent / H₂SO₄ / acetone; H₂O / 3 h / 20 °C

3.1: 95 percent / pyridine / 24 h / 50 °C

4.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

4.2: 99 percent / tetrabutylammonium bromide / tetrahydrofuran / 4 h / 20 °C

5.1: 96 percent / HBr / acetic acid / 10 - 15 °C

6.1: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

7.1: 100 percent / molecular sieves 4 Angstroem / CH₂Cl₂ / 3 h / 4 °C

8.1: 69 percent / BF₃*Et₂O / diethyl ether / -78 - 0 °C

With pyridine; 4 A molecular sieve; sulfuric acid; boron trifluoride diethyl etherate; hydrogen bromide; sodium hydride; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetic acid; acetone;

DOI:10.1021/jo0203903

upstream raw materials:

n-butyllithium

3,6-di-O-benzyl-4,5-O-isopropylidene-D-xylo-aldehydohexos-5-ulo-2,5-furanose N-benzylimine

benzyl bromide

2,3:4,6-bis-O-isopropylidene-L-sorbose