(R)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-but-3-yn-1-ol

Base Information

• Chemical Name: (R)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-but-3-yn-1-ol
• CAS No.: 188640-85-9
• Molecular Formula: C₁₈H₂₂O₅
• Molecular Weight: 318.37
• Mol file: 188640-85-9.mol

Synonyms:(R)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-but-3-yn-1-ol

Chemical Property of (R)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-but-3-yn-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-but-3-yn-1-ol

There total 2 articles about (R)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-but-3-yn-1-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: 80.0%

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) + propargyl bromide (106-96-7) → (R)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-but-3-yn-1-ol (188640-85-9)

Guidance literature:

With zinc; In tetrahydrofuran; for 3h; Ambient temperature;

DOI:10.1016/S0040-4020(96)01156-8

Reference yield: 61.0%

(3aR,5R,6S,6aR)-6-Benzyloxy-5-[(R)-1-(4-methoxy-benzyloxy)-but-3-ynyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole → (R)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-but-3-yn-1-ol (188640-85-9)

Guidance literature:

With manganese triacetate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1016/S0040-4039(00)01855-4

Reference yield: 92.0%

acetic anhydride (108-24-7) + (R)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-but-3-yn-1-ol (188640-85-9) → Acetic acid (R)-1-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-but-3-ynyl ester

Guidance literature:

With pyridine;

DOI:10.1016/S0040-4020(96)01156-8

upstream raw materials:

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

propargyl bromide

Downstream raw materials:

3-O-benzyl-1,2-O-isopropylidene-6,7,8-trideoxy-α-D-gluco-oct-7-enofuranose