C-(2,3,4-TRI-O-ACETYL-1-BROMO-1-DEOXY-ALPHA-D-ARABINOPYRANOSYL) FORMAMIDE

Base Information

• Chemical Name: C-(2,3,4-TRI-O-ACETYL-1-BROMO-1-DEOXY-ALPHA-D-ARABINOPYRANOSYL) FORMAMIDE
• CAS No.: 189633-63-4
• Molecular Formula: C₁₂H₁₆BrNO₈
• Molecular Weight: 382.165
• Mol file: 189633-63-4.mol

Synonyms:C-(2,3,4-TRI-O-ACETYL-1-BROMO-1-DEOXY-ALPHA-D-ARABINOPYRANOSYL) FORMAMIDE

Chemical Property of C-(2,3,4-TRI-O-ACETYL-1-BROMO-1-DEOXY-ALPHA-D-ARABINOPYRANOSYL) FORMAMIDE

Chemical Property:

• PSA: 111.92000
• LogP: 0.42648

Purity/Quality:

97% ^*data from raw suppliers

C-(2,3,4-TRI-O-ACETYL-1-BROMO-1-DEOXY-ALPHA-D-ARABINOPYRANOSYL) FORMAMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of C-(2,3,4-TRI-O-ACETYL-1-BROMO-1-DEOXY-ALPHA-D-ARABINOPYRANOSYL) FORMAMIDE

There total 1 articles about C-(2,3,4-TRI-O-ACETYL-1-BROMO-1-DEOXY-ALPHA-D-ARABINOPYRANOSYL) FORMAMIDE 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: 61.0%

2,3,4-tri-O-acetyl-1-deoxy-1-bromo-α-D-arabinopyranosyl cyanide (89158-09-8) → Acetic acid (2R,3S,4R,5R)-4,5-diacetoxy-2-bromo-2-carbamoyl-tetrahydro-pyran-3-yl ester (189633-63-4)

Guidance literature:

With water; titanium tetrachloride; In acetic acid; for 0.5h; 1) 0 deg C, 30 min, 2) room temperature, 2.5 d;

DOI:10.1016/S0040-4020(97)00213-5

Reference yield: 40.0%

silver cyanate (3315-16-0) + Acetic acid (2R,3S,4R,5R)-4,5-diacetoxy-2-bromo-2-carbamoyl-tetrahydro-pyran-3-yl ester (189633-63-4) → C-(2,3,4-tri-O-acetyl-1-hydroxy-α-D-arabinopyranosyl)formamide (189633-66-7) + (3R,4R,5S,6S)-3,4,5-triacetoxy-7,9-diaza-1-oxa-spiro[4,5]decane-8,10-dione (189633-64-5)

Guidance literature:

With molecular sieve; In nitromethane; at 80 ℃; for 3.5h;

DOI:10.1016/S0040-4020(97)00213-5

Reference yield: 35.0%

silver cyanate (3315-16-0) + Acetic acid (2R,3S,4R,5R)-4,5-diacetoxy-2-bromo-2-carbamoyl-tetrahydro-pyran-3-yl ester (189633-63-4) → C-(2,3,4-tri-O-acetyl-1-hydroxy-α-D-arabinopyranosyl)formamide (189633-66-7) + (3R,4R,5S,6R)-3,4,5-triacetoxy-7,9-diaza-1-oxa-spiro[4,5]decane-8,10-dione + (3R,4R,5S,6S)-3,4,5-triacetoxy-7,9-diaza-1-oxa-spiro[4,5]decane-8,10-dione (189633-64-5)

Guidance literature:

With molecular sieve; In nitromethane; at 80 ℃; for 3.5h;

DOI:10.1016/S0040-4020(97)00213-5

upstream raw materials:

2,3,4-tri-O-acetyl-1-deoxy-1-bromo-α-D-arabinopyranosyl cyanide

Downstream raw materials:

C-(2,3,4-tri-O-acetyl-1-hydroxy-α-D-arabinopyranosyl)formamide

(3R,4R,5S,6R)-3,4,5-triacetoxy-7,9-diaza-1-oxa-spiro[4,5]decane-10-one-8-thione

(3R,4R,5S,6S)-3,4,5-triacetoxy-7,9-diaza-1-oxa-spiro[4,5]decane-8,10-dione

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