5-BROMO-5-DEOXY-2,3-O-ISOPROPYLIDENE-D-RIBONOLACTONE

Base Information

• Chemical Name: 5-BROMO-5-DEOXY-2,3-O-ISOPROPYLIDENE-D-RIBONOLACTONE
• CAS No.: 94324-23-9
• Molecular Formula: C₈H₁₁BrO₄
• Molecular Weight: 251.077
• Hs Code.: 29322985
• Mol file: 94324-23-9.mol

Synonyms:Furo[3,4-d]-1,3-dioxole,D-ribonic acid deriv.

Chemical Property of 5-BROMO-5-DEOXY-2,3-O-ISOPROPYLIDENE-D-RIBONOLACTONE

Chemical Property:

• Vapor Pressure: 8.05E-05mmHg at 25°C
• Melting Point: 85-89oC
• Refractive Index: 1.4490 (estimate)
• Boiling Point: 341.4°C at 760 mmHg
• Flash Point: 160.3°C
• PSA: 44.76000
• Density: 1.519g/cm³
• LogP: 0.82680
• Storage Temp.: 0-6°C
• Solubility.: Acetone, Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

98%min ^*data from raw suppliers

5-Bromo-5-deoxy-2,3-O-isopropylidene-D-ribono-1,4-lactone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A key intermediate for the synthesis of olefinic optically active building blocks

Technology Process of 5-BROMO-5-DEOXY-2,3-O-ISOPROPYLIDENE-D-RIBONOLACTONE

There total 3 articles about 5-BROMO-5-DEOXY-2,3-O-ISOPROPYLIDENE-D-RIBONOLACTONE 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%

2,3-O-isopropylidene-D-ribonic-γ-lactone (30725-00-9) → 5-bromo-5-deoxy-2,3-O-isopropylidene-D-ribono-1,4-lactone (94324-23-9)

Guidance literature:

With N-Bromosuccinimide; triphenylphosphine;

Reference yield:

D-Ribono-1,4-lactone (5336-08-3) → 5-bromo-5-deoxy-2,3-O-isopropylidene-D-ribono-1,4-lactone (94324-23-9)

Guidance literature:

Multi-step reaction with 2 steps

1: SOBr₂ / dimethylformamide / 0 °C

2: I₂ / 20 °C

With sulfurous dibromide; iodine; In N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(02)00170-2

Reference yield:

acetone (67-64-1) + 5-bromo-5-deoxy-D-pentono-1,4-lactone (160456-85-9) → 5-bromo-5-deoxy-2,3-O-isopropylidene-D-ribono-1,4-lactone (94324-23-9)

Guidance literature:

With iodine; at 20 ℃;

DOI:10.1016/S0008-6215(02)00170-2

upstream raw materials:

2,3-O-isopropylidene-D-ribonic-γ-lactone

acetone

5-bromo-5-deoxy-D-pentono-1,4-lactone

D-Ribono-1,4-lactone

Downstream raw materials:

4,5-dideoxy-2,3-O-isopropylidene-D-erythro-pent-4-enonic acid

(3S,4S,5R)-3-amino-5-benzyloxy-N-[(1S)-1-(tert-butoxycarbonyl)-3-methylbutyl]-4-hydroxypiperidin-2-one

(S)-2-((3R,4S,5R)-5-Benzyloxy-3,4-dihydroxy-2-oxo-piperidin-1-yl)-4-methyl-pentanoic acid tert-butyl ester

(3S,4S,5R)-3-azido-5-benzyloxy-N-[(1S)-1-(tert-butoxycarbonyl)-3-methylbutyl]-4-hydroxypiperidin-2-one

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