2,6-anhydro-3,4,5-tri-O-benzyl-7-O-(trimethylacetyl)-aldehydo-L-glycero-L-gulo-heptose

Base Information

• Chemical Name: 2,6-anhydro-3,4,5-tri-O-benzyl-7-O-(trimethylacetyl)-aldehydo-L-glycero-L-gulo-heptose
• CAS No.: 133191-86-3
• Molecular Formula: C₃₃H₃₈O₇
• Molecular Weight: 546.661
• Mol file: 133191-86-3.mol

Synonyms:2,6-anhydro-3,4,5-tri-O-benzyl-7-O-(trimethylacetyl)-aldehydo-L-glycero-L-gulo-heptose

Chemical Property of 2,6-anhydro-3,4,5-tri-O-benzyl-7-O-(trimethylacetyl)-aldehydo-L-glycero-L-gulo-heptose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,6-anhydro-3,4,5-tri-O-benzyl-7-O-(trimethylacetyl)-aldehydo-L-glycero-L-gulo-heptose

There total 10 articles about 2,6-anhydro-3,4,5-tri-O-benzyl-7-O-(trimethylacetyl)-aldehydo-L-glycero-L-gulo-heptose 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: 86.0%

2,6-anhydro-3,4,5-tri-O-benzyl-1-O-(trimethylacetyl)-D-glycero-D-gulo-heptitol (133191-85-2) → 2,6-anhydro-3,4,5-tri-O-benzyl-7-O-(trimethylacetyl)-aldehydo-L-glycero-L-gulo-heptose (133191-86-3)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.25h;

DOI:10.1021/jo00002a009

Reference yield:

3,4,5,7-tetra-O-benzyl-1-O-(methoxymethyl)-α,β-D-gluco-2-heptulopyranose (133191-78-3,133191-90-9) → 2,6-anhydro-3,4,5-tri-O-benzyl-7-O-(trimethylacetyl)-aldehydo-L-glycero-L-gulo-heptose (133191-86-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 82 percent / concentrated HCl / 2 h / Heating

2: 87 percent / 6 M HCl / tetrahydrofuran / 1.5 h / 60 °C

3: 92 percent / pyridine / 1 h / 60 °C

4: 66 percent / Et₃SiH, BF₃*Et₂O / acetonitrile / 3 h / Ambient temperature

5: 100 percent / H₂ / 10percent Pd/C / acetic acid / 24 h / Ambient temperature

6: 79 percent / pyridine / 15 h / Ambient temperature

7: 82 percent / NaH / n-Bu₄NI / tetrahydrofuran; paraffin / 15 h / Ambient temperature

8: 71 percent / H₂SO₄ / methanol / 0.5 h / Ambient temperature

9: 86 percent / (COCl)2, DMSO / CH₂Cl₂ / 0.25 h / -78 °C

With pyridine; hydrogenchloride; triethylsilane; oxalyl dichloride; boron trifluoride diethyl etherate; hydrogen; sodium hydride; dimethyl sulfoxide; hydrogenchloride; palladium on activated charcoal; sulfuric acid; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; methanol; dichloromethane; acetic acid; acetonitrile; paraffin;

DOI:10.1021/jo00002a009

Reference yield:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) → 2,6-anhydro-3,4,5-tri-O-benzyl-7-O-(trimethylacetyl)-aldehydo-L-glycero-L-gulo-heptose (133191-86-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, -78 deg C, 30 min

2: 82 percent / concentrated HCl / 2 h / Heating

3: 87 percent / 6 M HCl / tetrahydrofuran / 1.5 h / 60 °C

4: 92 percent / pyridine / 1 h / 60 °C

5: 66 percent / Et₃SiH, BF₃*Et₂O / acetonitrile / 3 h / Ambient temperature

6: 100 percent / H₂ / 10percent Pd/C / acetic acid / 24 h / Ambient temperature

7: 79 percent / pyridine / 15 h / Ambient temperature

8: 82 percent / NaH / n-Bu₄NI / tetrahydrofuran; paraffin / 15 h / Ambient temperature

9: 71 percent / H₂SO₄ / methanol / 0.5 h / Ambient temperature

10: 86 percent / (COCl)2, DMSO / CH₂Cl₂ / 0.25 h / -78 °C

With pyridine; hydrogenchloride; triethylsilane; n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; hydrogen; sodium hydride; dimethyl sulfoxide; hydrogenchloride; palladium on activated charcoal; sulfuric acid; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; methanol; dichloromethane; acetic acid; acetonitrile; paraffin;

DOI:10.1021/jo00002a009

upstream raw materials:

2,6-anhydro-3,4,5-tri-O-benzyl-1-O-(trimethylacetyl)-D-glycero-D-gulo-heptitol

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

2,6-anhydro-1-O-(trimethylacetyl)-D-glycero-D-gulo-heptitol

2,6-anhydro-1-O-(trimethylacetyl)-7-O-(triphenylmethyl)-D-glycero-D-gulo-heptitol