(3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-((R)-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-yl)-tetrahydro-furo[2,3-d][1,3]dioxole

Base Information

• Chemical Name: (3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-((R)-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-yl)-tetrahydro-furo[2,3-d][1,3]dioxole
• CAS No.: 190733-40-5
• Molecular Formula: C₁₆H₂₀O₇S
• Molecular Weight: 356.397

Synonyms:(3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-((R)-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-yl)-tetrahydro-furo[2,3-d][1,3]dioxole

Chemical Property of (3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-((R)-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-yl)-tetrahydro-furo[2,3-d][1,3]dioxole

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Technology Process of (3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-((R)-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-yl)-tetrahydro-furo[2,3-d][1,3]dioxole

There total 1 articles about (3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-((R)-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-yl)-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: 89.0%

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) → (3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-((R)-2-oxo-2λ4-[1,3,2]dioxathiolan-4-yl)-tetrahydro-furo[2,3-d][1,3]dioxole (190733-40-5)

Guidance literature:

With thionyl chloride; triethylamine; In dichloromethane; at 0 ℃;

DOI:10.1021/jo962066b

Reference yield: 83.0%

(3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-((R)-2-oxo-2λ4-[1,3,2]dioxathiolan-4-yl)-tetrahydro-furo[2,3-d][1,3]dioxole (190733-40-5) → 3-O-benzyl 1,2-O-isopropylidene-5,6-O-sulfuryl-α-D-glucofuranose (158946-12-4)

Guidance literature:

With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; Ambient temperature;

DOI:10.1021/jo962066b

Reference yield:

(3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-((R)-2-oxo-2λ4-[1,3,2]dioxathiolan-4-yl)-tetrahydro-furo[2,3-d][1,3]dioxole (190733-40-5) → 5-S-acetyl-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-5-thio-β-L-idofuranose (190599-86-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 83 percent / NaIO₄, RuCl₃*3H₂O / acetonitrile; CCl₄; H₂O / Ambient temperature

2: 100 percent / acetone / Ambient temperature

3: 86 percent / NaOMe / methanol / Ambient temperature

4: 66 percent / LiAlH₄ / tetrahydrofuran / Ambient temperature

5: 87 percent / pyridine / Ambient temperature

With ruthenium trichloride; sodium periodate; lithium aluminium tetrahydride; sodium methylate; In tetrahydrofuran; pyridine; methanol; tetrachloromethane; water; acetone; acetonitrile;

DOI:10.1021/jo962066b

upstream raw materials:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

Downstream raw materials:

3-O-benzyl 1,2-O-isopropylidene-5,6-O-sulfuryl-α-D-glucofuranose

(R)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-hydroxy-1-trimethylsilanyl-propan-1-one

(R)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(2-trimethylsilanyl-[1,3]dithian-2-yl)-ethanol

3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose

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