(2R,4R)-4-(benzyloxy)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3,3-difluorobutane-1,2-diol

Base Information

• Chemical Name: (2R,4R)-4-(benzyloxy)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3,3-difluorobutane-1,2-diol
• CAS No.: 634181-79-6
• Molecular Formula: C₁₆H₂₂F₂O₅
• Molecular Weight: 332.344

Synonyms:(2R,4R)-4-(benzyloxy)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3,3-difluorobutane-1,2-diol

Chemical Property of (2R,4R)-4-(benzyloxy)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3,3-difluorobutane-1,2-diol

Chemical Property:

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Technology Process of (2R,4R)-4-(benzyloxy)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3,3-difluorobutane-1,2-diol

There total 8 articles about (2R,4R)-4-(benzyloxy)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3,3-difluorobutane-1,2-diol 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: 75.0%

(R)-4-((R)-1-(benzyloxy)-2,2-difluorobut-3-en-1-yl)-2,2-dimethyl-1,3-dioxolane (634181-78-5) → (2R,4R)-4-(benzyloxy)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3,3-difluorobutane-1,2-diol (634181-79-6)

Guidance literature:

With potassium osmate(VI) dihydrate; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); potassium carbonate; potassium hexacyanoferrate(III); In water; tert-butyl alcohol; at 0 ℃; for 24h;

Reference yield: 47.5%

(R)-4-((R)-1-(benzyloxy)-2,2-difluorobut-3-en-1-yl)-2,2-dimethyl-1,3-dioxolane (634181-78-5) → (2R,4R)-4-(benzyloxy)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3,3-difluorobutane-1,2-diol (634181-79-6) + (2R,3R,5S)-3-O-benzyl-4,4-difluoro-1,2-O-isopropylidenehexane-1,2,3,5,6-pentol (634181-80-9)

Guidance literature:

With osmium(VIII) oxide; bis-(2-chloro-ethyl)-methyl-amine oxide; water; In acetone; at 20 ℃; for 48h;

DOI:10.1021/jo034512i

Reference yield:

2,3-isopropylidene-glyceraldehyde (15186-48-8) → (2R,4R)-4-(benzyloxy)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3,3-difluorobutane-1,2-diol (634181-79-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: indium / dimethylformamide

1.2: sodium hydride; Bu₄NI / tetrahydrofuran / 0.83 h / 0 - 20 °C

1.3: tetrahydrofuran / 20 °C

2.1: 1.052 g / NMNO / OsO₄ / acetone; H₂O / 48 h / 20 °C

With indium; bis-(2-chloro-ethyl)-methyl-amine oxide; osmium(VIII) oxide; In water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.jfluchem.2007.01.007

upstream raw materials:

(R)-4-((R)-1-(benzyloxy)-2,2-difluorobut-3-en-1-yl)-2,2-dimethyl-1,3-dioxolane

benzyl bromide

2,3-isopropylidene-glyceraldehyde

Downstream raw materials:

(2R,4R)-2-benzyloxy-5-benzoyloxy-3,3-difluoropentane-1,4-diol

1-O-acetyl-2-O-benzyl-5-O-benzoyl-3-deoxy-3,3-difluoro-α-D-arabinofuranose

N¹-(2-O-benzyl-3-deoxy-3,3-difluoro-β-D-arabinofuranosyl)cytosine

N¹-(2-O-benzyl-3-deoxy-3,3-difluoro-α-D-arabinofuranosyl)cytosine

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