(3aR,4R,6R,7aS)-4-Allyl-6-(3-benzyloxy-propyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

Base Information

• Chemical Name: (3aR,4R,6R,7aS)-4-Allyl-6-(3-benzyloxy-propyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran
• CAS No.: 169895-74-3
• Molecular Formula: C₂₁H₃₀O₄
• Molecular Weight: 346.467
• Mol file: 169895-74-3.mol

Synonyms:(3aR,4R,6R,7aS)-4-Allyl-6-(3-benzyloxy-propyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

Chemical Property of (3aR,4R,6R,7aS)-4-Allyl-6-(3-benzyloxy-propyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4R,6R,7aS)-4-Allyl-6-(3-benzyloxy-propyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

There total 1 articles about (3aR,4R,6R,7aS)-4-Allyl-6-(3-benzyloxy-propyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran 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: 98.0%

benzyl bromide (100-39-0) + 3-((3aR,4R,6R,7aS)-4-Allyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-propan-1-ol (132375-60-1) → (3aR,4R,6R,7aS)-4-Allyl-6-(3-benzyloxy-propyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran (169895-74-3)

Guidance literature:

With potassium hydride; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1021/jo9807619

Reference yield: 100.0%

(3aR,4R,6R,7aS)-4-Allyl-6-(3-benzyloxy-propyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran (169895-74-3) → (2R,3S,4S,6R)-2-Allyl-6-(3-benzyloxy-propyl)-tetrahydro-pyran-3,4-diol (169895-44-7)

Guidance literature:

With hydrogenchloride; In methanol; for 5h; Ambient temperature;

DOI:10.1021/jo9807619

Reference yield:

(3aR,4R,6R,7aS)-4-Allyl-6-(3-benzyloxy-propyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran (169895-74-3) → (2R,3S,4S,6R)-2-Allyl-4-benzyloxy-6-(3-benzyloxy-propyl)-tetrahydro-pyran-3-ol (169895-45-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / HCl / methanol / 5 h / Ambient temperature

2: 1.) Bu₂SnO, 2.) CsF / 1.) MeOH, reflux, 1.5 h, 2.) DMF, rt, 12 h

With hydrogenchloride; di(n-butyl)tin oxide; cesium fluoride; In methanol;

DOI:10.1021/jo9807619

upstream raw materials:

benzyl bromide

3-((3aR,4R,6R,7aS)-4-Allyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-propan-1-ol

Downstream raw materials:

(2R,3S,4S,6R)-2-Allyl-4-benzyloxy-6-(3-benzyloxy-propyl)-tetrahydro-pyran-3-ol

(2R,3S,4S,6R)-2-Allyl-6-(3-benzyloxy-propyl)-tetrahydro-pyran-3,4-diol

(E)-3-[(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-2-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acrylic acid methyl ester

(E)-3-[(2R,3S,4aR,6R,8S,8aS)-3-Acetoxy-8-benzyloxy-6-(3-benzyloxy-propyl)-2-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acrylic acid methyl ester