(2R,4R)-4-Benzyloxy-5-((4R,5R)-4,5-dimethyl-[1,3]dioxolan-2-yl)-1-methoxy-5-methyl-hexan-2-ol

Base Information

• Chemical Name: (2R,4R)-4-Benzyloxy-5-((4R,5R)-4,5-dimethyl-[1,3]dioxolan-2-yl)-1-methoxy-5-methyl-hexan-2-ol
• CAS No.: 73804-17-8
• Molecular Formula: C₂₀H₃₂O₅
• Molecular Weight: 352.471
• Mol file: 73804-17-8.mol

Synonyms:

Chemical Property of (2R,4R)-4-Benzyloxy-5-((4R,5R)-4,5-dimethyl-[1,3]dioxolan-2-yl)-1-methoxy-5-methyl-hexan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4R)-4-Benzyloxy-5-((4R,5R)-4,5-dimethyl-[1,3]dioxolan-2-yl)-1-methoxy-5-methyl-hexan-2-ol

There total 7 articles about (2R,4R)-4-Benzyloxy-5-((4R,5R)-4,5-dimethyl-[1,3]dioxolan-2-yl)-1-methoxy-5-methyl-hexan-2-ol 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:

(R)-4-Benzyloxy-5-((4R,5R)-4,5-dimethyl-[1,3]dioxolan-2-yl)-1-methoxy-5-methyl-hexan-2-one (73787-18-5) → (2R,4R)-4-Benzyloxy-5-((4R,5R)-4,5-dimethyl-[1,3]dioxolan-2-yl)-1-methoxy-5-methyl-hexan-2-ol (73804-17-8) + (2S,4R)-4-Benzyloxy-5-((4R,5R)-4,5-dimethyl-[1,3]dioxolan-2-yl)-1-methoxy-5-methyl-hexan-2-ol (73787-17-4)

Guidance literature:

With lithium tri-t-butoxyaluminum hydride; In diethyl ether; at -78 ℃; for 0.5h; Yield given. Title compound not separated from byproducts;

DOI:10.1016/S0040-4039(00)88690-6

Reference yield:

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) → (2R,4R)-4-Benzyloxy-5-((4R,5R)-4,5-dimethyl-[1,3]dioxolan-2-yl)-1-methoxy-5-methyl-hexan-2-ol (73804-17-8)

Guidance literature:

Multi-step reaction with 6 steps

1: p-TsOH*H₂O / benzene / 8 h / Heating

2: 64 percent / PCC, NaOAc / CH₂Cl₂ / 12 h / Ambient temperature

3: 2.) Jones reagent / 1.) ether, 12 h at r.t.; 2.) acetone, 30 min at 0 deg C

4: 1.) LiAlH₄; 2.) t-AmONa / 1.) ether, toluene, 2 h at -123 deg C; 2.) DMSO, 2 h at r.t.

5: 99 percent / mCPBA / CH₂Cl₂ / 12 h / Ambient temperature

6: NaOMe / benzene / 48 h / Ambient temperature

With lithium aluminium tetrahydride; jones reagent; sodium methylate; sodium acetate; sodium tert-pentoxide; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In dichloromethane; benzene;

DOI:10.1016/0040-4020(84)80017-4

Reference yield:

2-((4R,5R)-4,5-Dimethyl-[1,3]dioxolan-2-yl)-2-methyl-hex-5-en-3-one (73787-13-0) → (2R,4R)-4-Benzyloxy-5-((4R,5R)-4,5-dimethyl-[1,3]dioxolan-2-yl)-1-methoxy-5-methyl-hexan-2-ol (73804-17-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) LiAlH₄; 2.) t-AmONa / 1.) ether, toluene, 2 h at -123 deg C; 2.) DMSO, 2 h at r.t.

2: 99 percent / mCPBA / CH₂Cl₂ / 12 h / Ambient temperature

3: NaOMe / benzene / 48 h / Ambient temperature

With lithium aluminium tetrahydride; sodium methylate; sodium tert-pentoxide; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; benzene;

DOI:10.1016/0040-4020(84)80017-4

upstream raw materials:

(R)-4-Benzyloxy-5-((4R,5R)-4,5-dimethyl-[1,3]dioxolan-2-yl)-1-methoxy-5-methyl-hexan-2-one

2,2-dimethyl-3-hydroxypropionaldehyde

2-((4R,5R)-4,5-Dimethyl-[1,3]dioxolan-2-yl)-2-methyl-hex-5-en-3-one

2-((4R,5R)-4,5-Dimethyl-[1,3]dioxolan-2-yl)-2-methyl-propan-1-ol