cis-syn-cis-4α,5α-O-isopropylidene-6α-benzyloxy-8α-methyl-3-oxatricyclo[3.2.0.0^2,6]decane

Base Information

• Chemical Name: cis-syn-cis-4α,5α-O-isopropylidene-6α-benzyloxy-8α-methyl-3-oxatricyclo[3.2.0.0^2,6]decane
• CAS No.: 370888-71-4
• Molecular Formula: C₂₀H₂₆O₄
• Molecular Weight: 330.424

Synonyms:cis-syn-cis-4α,5α-O-isopropylidene-6α-benzyloxy-8α-methyl-3-oxatricyclo[3.2.0.0^2,6]decane

Chemical Property of cis-syn-cis-4α,5α-O-isopropylidene-6α-benzyloxy-8α-methyl-3-oxatricyclo[3.2.0.0^2,6]decane

Chemical Property:

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Technology Process of cis-syn-cis-4α,5α-O-isopropylidene-6α-benzyloxy-8α-methyl-3-oxatricyclo[3.2.0.0^2,6]decane

There total 6 articles about cis-syn-cis-4α,5α-O-isopropylidene-6α-benzyloxy-8α-methyl-3-oxatricyclo[3.2.0.0^2,6]decane 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: 77.0%

(3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-6-(2-methyl-allyl)-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxole (370888-69-0) → cis-syn-cis-4α,5α-O-isopropylidene-6α-benzyloxy-8α-methyl-3-oxatricyclo[3.2.0.02,6]decane (370888-71-4)

Guidance literature:

With copper(I) triflate; In diethyl ether; for 3.5h; Irradiation;

DOI:10.1021/jo026920c

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-ribo-3-hexulofuranose (2847-00-9) → cis-syn-cis-4α,5α-O-isopropylidene-6α-benzyloxy-8α-methyl-3-oxatricyclo[3.2.0.02,6]decane (370888-71-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Mg / tetrahydrofuran

1.2: 70 percent / tetrahydrofuran / 6 h / 20 °C

2.1: 80 percent / NaH / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / Heating

3.1: aqueous acetic acid / 12 h / 20 °C

4.1: 840 mg / imidazole; PPh₃; iodine / toluene / 2 h / Heating

5.1: 77 percent / CuOTf / diethyl ether / 3.5 h / Irradiation

With 1H-imidazole; iodine; copper(I) triflate; sodium hydride; magnesium; acetic acid; triphenylphosphine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; toluene;

DOI:10.1021/jo026920c

Reference yield:

1:2,5:6-di-O-isopropylidene-3-C-(2'-methyl-2'-propenyl)-α-D-allofuranose → cis-syn-cis-4α,5α-O-isopropylidene-6α-benzyloxy-8α-methyl-3-oxatricyclo[3.2.0.02,6]decane (370888-71-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / NaH / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / Heating

2: aqueous acetic acid / 12 h / 20 °C

3: 840 mg / imidazole; PPh₃; iodine / toluene / 2 h / Heating

4: 77 percent / CuOTf / diethyl ether / 3.5 h / Irradiation

With 1H-imidazole; iodine; copper(I) triflate; sodium hydride; acetic acid; triphenylphosphine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; toluene;

DOI:10.1021/jo026920c

upstream raw materials:

(3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-6-(2-methyl-allyl)-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxole

benzyl bromide

1,2:5,6-di-O-isopropylidene-α-D-ribo-3-hexulofuranose

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