5-benzyloxy-2-desoxy-1-hydroxy-3-hydroxy-α-D-lyxose

Base Information

• Chemical Name: 5-benzyloxy-2-desoxy-1-hydroxy-3-hydroxy-α-D-lyxose
• CAS No.: 1583259-76-0
• Molecular Formula: C₁₂H₁₆O₄
• Molecular Weight: 224.257
• Mol file: 1583259-76-0.mol

Synonyms:

Chemical Property of 5-benzyloxy-2-desoxy-1-hydroxy-3-hydroxy-α-D-lyxose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-benzyloxy-2-desoxy-1-hydroxy-3-hydroxy-α-D-lyxose

There total 6 articles about 5-benzyloxy-2-desoxy-1-hydroxy-3-hydroxy-α-D-lyxose 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:

5-benzyloxy-2-desoxy-3-hydroxy-D-lyxolactone (103927-52-2) → 5-benzyloxy-2-desoxy-1-hydroxy-3-hydroxy-β-D-lyxose (1583259-77-1) + 5-benzyloxy-2-desoxy-1-hydroxy-3-hydroxy-α-D-lyxose (1583259-76-0)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 ℃; for 2h; Overall yield = 75 %; Overall yield = 42.3 mg; diastereoselective reaction;

DOI:10.1021/ja502205q

Reference yield:

3-Benzyloxypropanal (19790-60-4) → 5-benzyloxy-2-desoxy-1-hydroxy-3-hydroxy-β-D-lyxose (1583259-77-1) + 5-benzyloxy-2-desoxy-1-hydroxy-3-hydroxy-α-D-lyxose (1583259-76-0)

Guidance literature:

Multi-step reaction with 4 steps

1: copper dichloride; (R)-5-((1-Benzyl-1H-indol-3-yl)methyl)-2,2,3-trimethylimidazolin-4-one tetrafluoroboric acid / ethyl acetate / 24 h / -30 °C / Molecular sieve

2: titanium(IV) dichlorodiisopropylate; boron trifluoride diethyl etherate / dichloromethane / 16 h / -40 °C / Inert atmosphere

3: zinc; water; trifluoroacetic acid / toluene / 32 h / 20 °C

4: diisobutylaluminium hydride / toluene / 2 h / -78 °C

With titanium(IV) dichlorodiisopropylate; boron trifluoride diethyl etherate; (R)-5-((1-Benzyl-1H-indol-3-yl)methyl)-2,2,3-trimethylimidazolin-4-one tetrafluoroboric acid; water; diisobutylaluminium hydride; trifluoroacetic acid; copper dichloride; zinc; In dichloromethane; ethyl acetate; toluene; 2: |Mukaiyama Aldol Addition;

DOI:10.1021/ja502205q

Reference yield:

benzyl bromide (100-39-0) → 5-benzyloxy-2-desoxy-1-hydroxy-3-hydroxy-β-D-lyxose (1583259-77-1) + 5-benzyloxy-2-desoxy-1-hydroxy-3-hydroxy-α-D-lyxose (1583259-76-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C

1.2: 16 h / 20 °C

2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 16 h / 20 °C

3.1: copper dichloride; CHF₃O₃S*C₁₃H₁₈N₂O / diethyl ether / 48 h / -30 °C / Molecular sieve; Inert atmosphere

4.1: titanium(IV) dichlorodiisopropylate; boron trifluoride diethyl etherate / dichloromethane / 16 h / -40 °C / Inert atmosphere

5.1: zinc; water; trifluoroacetic acid / toluene / 32 h / 20 °C

6.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C

With titanium(IV) dichlorodiisopropylate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; CHF₃O₃S*C₁₃H₁₈N₂O; boron trifluoride diethyl etherate; water; sodium hydride; diisobutylaluminium hydride; trifluoroacetic acid; copper dichloride; zinc; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil; 4.1: |Mukaiyama Aldol Addition;

DOI:10.1021/ja502205q

upstream raw materials:

(3R,4R)-isopropyl 5-(benzyloxy)-3-hydroxy-4-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)pentanoate

5-benzyloxy-2-desoxy-3-hydroxy-D-lyxolactone

(R)-3-(benzyloxy)-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)propanal

3-Benzyloxypropanal