2,6-anhydro-3,4,5-tri-O-benzyl-1-O-(trimethylacetyl)-7-O-(triphenylmethyl)-D-glycero-D-gulo-heptitol

Base Information

Chemical Name:2,6-anhydro-3,4,5-tri-O-benzyl-1-O-(trimethylacetyl)-7-O-(triphenylmethyl)-D-glycero-D-gulo-heptitol
CAS No.:133191-84-1
Molecular Formula:C₅₂H₅₄O₇
Molecular Weight:790.997
Hs Code.:

Synonyms:2,6-anhydro-3,4,5-tri-O-benzyl-1-O-(trimethylacetyl)-7-O-(triphenylmethyl)-D-glycero-D-gulo-heptitol

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Chemical Property of 2,6-anhydro-3,4,5-tri-O-benzyl-1-O-(trimethylacetyl)-7-O-(triphenylmethyl)-D-glycero-D-gulo-heptitol

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Technology Process of 2,6-anhydro-3,4,5-tri-O-benzyl-1-O-(trimethylacetyl)-7-O-(triphenylmethyl)-D-glycero-D-gulo-heptitol

There total 8 articles about 2,6-anhydro-3,4,5-tri-O-benzyl-1-O-(trimethylacetyl)-7-O-(triphenylmethyl)-D-glycero-D-gulo-heptitol 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: 82.0%

: 100-39-0
benzyl bromide

: 133191-83-0
2,6-anhydro-1-O-(trimethylacetyl)-7-O-(triphenylmethyl)-D-glycero-D-gulo-heptitol

: 133191-84-1
2,6-anhydro-3,4,5-tri-O-benzyl-1-O-(trimethylacetyl)-7-O-(triphenylmethyl)-D-glycero-D-gulo-heptitol

Guidance literature:: With sodium hydride; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; paraffin; for 15h; Ambient temperature;
DOI:10.1021/jo00002a009

Reference yield:

: 133191-78-3,133191-90-9
3,4,5,7-tetra-O-benzyl-1-O-(methoxymethyl)-α,β-D-gluco-2-heptulopyranose

: 133191-84-1
2,6-anhydro-3,4,5-tri-O-benzyl-1-O-(trimethylacetyl)-7-O-(triphenylmethyl)-D-glycero-D-gulo-heptitol

Guidance literature:: Multi-step reaction with 7 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

With pyridine; hydrogenchloride; triethylsilane; boron trifluoride diethyl etherate; hydrogen; sodium hydride; hydrogenchloride; palladium on activated charcoal; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; acetic acid; acetonitrile; paraffin;
DOI:10.1021/jo00002a009

Reference yield:

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 133191-84-1
2,6-anhydro-3,4,5-tri-O-benzyl-1-O-(trimethylacetyl)-7-O-(triphenylmethyl)-D-glycero-D-gulo-heptitol

Guidance literature:: Multi-step reaction with 8 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

With pyridine; hydrogenchloride; triethylsilane; n-butyllithium; boron trifluoride diethyl etherate; hydrogen; sodium hydride; hydrogenchloride; palladium on activated charcoal; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; acetic acid; acetonitrile; paraffin;
DOI:10.1021/jo00002a009