3,7-anhydro-4,5,6-tri-O-benzyl-1,2,8-trideoxy-D-gulo-oct-1,7-dienitol

Base Information

• Chemical Name: 3,7-anhydro-4,5,6-tri-O-benzyl-1,2,8-trideoxy-D-gulo-oct-1,7-dienitol
• CAS No.: 261956-04-1
• Molecular Formula: C₂₉H₃₀O₄
• Molecular Weight: 442.555
• Mol file: 261956-04-1.mol

Synonyms:3,7-anhydro-4,5,6-tri-O-benzyl-1,2,8-trideoxy-D-gulo-oct-1,7-dienitol

Chemical Property of 3,7-anhydro-4,5,6-tri-O-benzyl-1,2,8-trideoxy-D-gulo-oct-1,7-dienitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,7-anhydro-4,5,6-tri-O-benzyl-1,2,8-trideoxy-D-gulo-oct-1,7-dienitol

There total 11 articles about 3,7-anhydro-4,5,6-tri-O-benzyl-1,2,8-trideoxy-D-gulo-oct-1,7-dienitol 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: 90.0%

3,7-anhydro-4,5,6-tri-O-benzyl-8-bromo-1,2,8-trideoxy-D-glycero-D-gulo-oct-1-enitol (854654-14-1) → 3,7-anhydro-4,5,6-tri-O-benzyl-1,2,8-trideoxy-D-gulo-oct-1,7-dienitol (261956-04-1)

Guidance literature:

With silver fluoride; In pyridine; at 20 ℃; for 72h;

DOI:10.1002/ejoc.200600455

Reference yield: 87.0%

Toluene-4-sulfonic acid (2R,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-ylmethyl ester (343315-86-6) → 3,7-anhydro-4,5,6-tri-O-benzyl-1,2,8-trideoxy-D-gulo-oct-1,7-dienitol (261956-04-1)

Guidance literature:

With 4 A molecular sieve; tetra-(n-butyl)ammonium iodide; sodium iodide; In dimethyl sulfoxide; at 80 ℃; for 1h;

DOI:10.1002/1099-0690(200103)2001:6<1053::aid-ejoc1053>3.3.co;2-j

Reference yield:

3,7-anhydro-1,2-dideoxy-D-glycero-D-gulo-oct-1-enitol (51450-27-2) → 3,7-anhydro-4,5,6-tri-O-benzyl-1,2,8-trideoxy-D-gulo-oct-1,7-dienitol (261956-04-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 49 percent / pyridine / 48 h / 20 °C

2.1: sodium hydride / dimethylformamide / 2 h / 20 °C

2.2: 61 percent / sodium bromide / dimethylformamide / 80 °C

3.1: 90 percent / silver fluoride / pyridine / 72 h / 20 °C

With pyridine; silver fluoride; sodium hydride; In pyridine; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200600455

upstream raw materials:

Toluene-4-sulfonic acid (2R,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-ylmethyl ester

3,7-anhydro-4,5,6-tri-O-benzyl-8-bromo-1,2,8-trideoxy-D-glycero-D-gulo-oct-1-enitol

3,7-anhydro-1,2-dideoxy-D-glycero-D-gulo-oct-1-enitol

4,5,6,8-Tetra-O-acetyl-3,7-anhydro-1,2-didesoxy-β-D-gluco-oct-1-enitol

Downstream raw materials:

((1R,2S,3R,4R,5S)-2,3,4-Tris-benzyloxy-5-methoxy-cyclooctyl)-methanol

((1S,2S,3R,4R,5S)-2,3,4-Tris-benzyloxy-5-methoxy-cyclooctyl)-methanol

(1S,2R,3R,4R)-2,3,4-tribenzyloxy-1-methoxy-5-methylenecyclooctane

(1R,2S,3R,4R,5S)-2,3,4-tribenzyloxy-5-methoxycycloocta-1-ol