(3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-octadecyloxymethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Base Information

• Chemical Name: (3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-octadecyloxymethyl-tetrahydro-furo[2,3-d][1,3]dioxole
• CAS No.: 87060-31-9
• Molecular Formula: C₃₃H₅₆O₅
• Molecular Weight: 532.805

Synonyms:(3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-octadecyloxymethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Chemical Property of (3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-octadecyloxymethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Chemical Property:

Purity/Quality:

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Technology Process of (3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-octadecyloxymethyl-tetrahydro-furo[2,3-d][1,3]dioxole

There total 6 articles about (3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-octadecyloxymethyl-tetrahydro-furo[2,3-d][1,3]dioxole 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: 86.0%

3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose (34370-91-7,59358-33-7,68354-70-1,70798-12-8,19139-80-1) + 1-Bromooctadecane (112-89-0) → (3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-octadecyloxymethyl-tetrahydro-furo[2,3-d][1,3]dioxole (87060-31-9)

Guidance literature:

With sodium hydroxide; (n-But)4HSO₄,50percent NaOH; at 70 ℃; for 24h;

DOI:10.1016/S0040-4039(00)88010-7

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (350255-13-9) → (3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-octadecyloxymethyl-tetrahydro-furo[2,3-d][1,3]dioxole (87060-31-9)

Guidance literature:

Multi-step reaction with 5 steps

1: (n-But)4NI,NaH / tetrahydrofuran

2: 0.8 percent H₂SO₄ / methanol / 24 h

3: NaI₄ / dioxane; H₂O

4: NaBH₄ / ethanol

5: 86 percent / (n-But)4HSO₄,50percent NaOH / 24 h / 70 °C

With sodium hydroxide; sodium tetrahydroborate; (n-But)4HSO₄,50percent NaOH; sulfuric acid; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; water;

DOI:10.1016/S0040-4039(00)88010-7

Reference yield:

benzyl bromide (100-39-0) → (3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-octadecyloxymethyl-tetrahydro-furo[2,3-d][1,3]dioxole (87060-31-9)

Guidance literature:

Multi-step reaction with 5 steps

1: (n-But)4NI,NaH / tetrahydrofuran

2: 0.8 percent H₂SO₄ / methanol / 24 h

3: NaI₄ / dioxane; H₂O

4: NaBH₄ / ethanol

5: 86 percent / (n-But)4HSO₄,50percent NaOH / 24 h / 70 °C

With sodium hydroxide; sodium tetrahydroborate; (n-But)4HSO₄,50percent NaOH; sulfuric acid; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; water;

DOI:10.1016/S0040-4039(00)88010-7

upstream raw materials:

3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

1-Bromooctadecane

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

benzyl bromide

Downstream raw materials:

C₄₁H₇₀NO₇P

(2R,3R)-2,3-Bis-benzyloxy-4-octadecyloxy-butan-1-ol

(2R,3R)-3-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-octadecyloxy-butan-2-ol

(2R,3R)-2-Benzyloxy-4-octadecyloxy-butane-1,3-diol

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