5-CHLOROACETOXY-2-BENZYLOXYISOSORBIDE

Base Information

• Chemical Name: 5-CHLOROACETOXY-2-BENZYLOXYISOSORBIDE
• CAS No.: 399534-53-3
• Molecular Formula: C15H17 Cl O5
• Molecular Weight: 312.75
• Mol file: 399534-53-3.mol

Synonyms:5-Chloroacetoxy-2-benzyloxyisosorbide, 1,4:3,6-Dianhydro-2-O-benzyl-D-glucitol chloroacetate

Chemical Property of 5-CHLOROACETOXY-2-BENZYLOXYISOSORBIDE

Chemical Property:

• Refractive Index: n20/D 1.537(lit.)
• Boiling Point: 343-344 °C(lit.)
• Flash Point: 110 °C
• PSA: 53.99000
• Density: 1.316 g/mL at 25 °C(lit.)
• LogP: 1.52000

Purity/Quality:

5-Chloroacetyl-2-benzylisosorbide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26-36

MSDS Files:

Total 1 MSDS from other Authors

Useful:

Technology Process of 5-CHLOROACETOXY-2-BENZYLOXYISOSORBIDE

There total 3 articles about 5-CHLOROACETOXY-2-BENZYLOXYISOSORBIDE 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: 84.0%

(3R,3aR,6S,6aR)-6-(Benzyloxy)hexahydrofuro[3,2-b]furan-3-ol (111956-66-2) + Chloroacetic anhydride (541-88-8) → Chloro-acetic acid (3R,3aR,6S,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester (399534-53-3)

Guidance literature:

With pyridine; In chloroform; at 20 ℃; for 12h;

DOI:10.1021/ol006651h

Reference yield:

benzyl bromide (100-39-0) → Chloro-acetic acid (3R,3aR,6S,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester (399534-53-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / NaH / dimethylformamide / 15 h / 20 °C

2: 84 percent / pyridine / CHCl₃ / 12 h / 20 °C

With pyridine; sodium hydride; In chloroform; N,N-dimethyl-formamide;

DOI:10.1021/ol006651h

Reference yield:

benzyl bromide (100-39-0) → Chloro-acetic acid (3R,3aR,6S,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester (399534-53-3)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 12 h

With pyridine;

DOI:10.1016/j.tetasy.2003.07.006

upstream raw materials:

(3R,3aR,6S,6aR)-6-(Benzyloxy)hexahydrofuro[3,2-b]furan-3-ol

Chloroacetic anhydride

benzyl bromide

Downstream raw materials:

(Triphenyl-λ⁵-phosphanylidene)-acetic acid (3aR,5R,6S,6aR)-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

((1R,2S)-2-Hydroxy-cyclopentyl)-acetic acid (3R,3aR,6S,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester

(E)-7-Oxo-hept-2-enoic acid (3R,3aR,6S,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester

Chloro-acetic acid (3aR,5R,6S,6aR)-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

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