benzyl [fluoro 3-deoxy-4,5-7,8-di-O-isopropylidene-α-D-manno-octulopyranosid]onate

Base Information

• Chemical Name: benzyl [fluoro 3-deoxy-4,5-7,8-di-O-isopropylidene-α-D-manno-octulopyranosid]onate
• CAS No.: 114827-01-9
• Molecular Formula: C₂₁H₂₇FO₇
• Molecular Weight: 410.44
• Mol file: 114827-01-9.mol

Synonyms:benzyl [fluoro 3-deoxy-4,5-7,8-di-O-isopropylidene-α-D-manno-octulopyranosid]onate

Chemical Property of benzyl [fluoro 3-deoxy-4,5-7,8-di-O-isopropylidene-α-D-manno-octulopyranosid]onate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl [fluoro 3-deoxy-4,5-7,8-di-O-isopropylidene-α-D-manno-octulopyranosid]onate

There total 10 articles about benzyl [fluoro 3-deoxy-4,5-7,8-di-O-isopropylidene-α-D-manno-octulopyranosid]onate 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: 50.0%

benzyl [3-deoxy-4,5-7,8-di-O-isopropylidene-α-D-manno-octulopyranosid]onate → benzyl [fluoro 3-deoxy-4,5-7,8-di-O-isopropylidene-α-D-manno-octulopyranosid]onate (114827-01-9)

Guidance literature:

With diethylamino-sulfur trifluoride; In dichloromethane; at -50 ℃; for 0.25h; Inert atmosphere; Molecular sieve;

DOI:10.1021/ja306274v

Reference yield: 42.0%

benzyl (2-O-acetyl-3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-oct-2-ulopyranosyl)onate → benzyl [fluoro 3-deoxy-4,5-7,8-di-O-isopropylidene-α-D-manno-octulopyranosid]onate (114827-01-9)

Guidance literature:

With pyridine; pyridine hydrogenfluoride; In dichloromethane; at -70 - 20 ℃;

DOI:10.1002/chem.202100837

Reference yield:

benzyl [2-1,3-dithiane-3-deoxy-4,5-7,8-di-O-isopropylidene-α-D-manno-octulopyranosid]onate (1392224-88-2) → benzyl [fluoro 3-deoxy-4,5-7,8-di-O-isopropylidene-α-D-manno-octulopyranosid]onate (114827-01-9)

Guidance literature:

Multi-step reaction with 2 steps

1: water; N-Bromosuccinimide / acetone / 0.17 h / 0 °C / Inert atmosphere

2: diethylamino-sulfur trifluoride / dichloromethane / 0.25 h / -50 °C / Inert atmosphere; Molecular sieve

With N-Bromosuccinimide; diethylamino-sulfur trifluoride; water; In dichloromethane; acetone;

DOI:10.1021/ja306274v

upstream raw materials:

benzyl [2-1,3-dithiane-3-deoxy-4,5-7,8-di-O-isopropylidene-α-D-manno-octulopyranosid]onate

2,3,5,6-di-isopropyIidene-1,4-dihydroxy-D-mannitol

2,3-5,6-di-O-isopropylidene-1,4-O-sulfate-D-mannitol

2,3:5,6-di-O-isopropylidene-D-mannitol 1,4-sulfite

Downstream raw materials:

C₁₁₈H₁₇₉N₂O₂₇P

C₉₆H₁₅₂NO₂₁P

benzyl [N-benzyloxycarbonyl-3-amino-propyl 4-O-benzyl-3-deoxy-7,8-O-isopropylidene-α-D-manno-octulopyranosid] onate

benzyl [N-benzyloxycarbonyl-3-amino-propyl 3-deoxy-4,5-7,8-di-O-isopropylidene-α-D-mannooctulopyranosid]onate