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

Base Information

Chemical Name:2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-O-(trimethylacetyl)-D-glycero-D-gulo-heptitol
CAS No.:133191-81-8
Molecular Formula:C₄₀H₄₆O₇
Molecular Weight:638.801
Hs Code.:

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

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

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

There total 5 articles about 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-O-(trimethylacetyl)-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: 66.0%

: 133191-80-7
3,4,5,7-tetra-O-benzyl-1-O-(trimethylacetyl)-α-D-gluco-2-heptulopyranose

: 133191-81-8
2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-O-(trimethylacetyl)-D-glycero-D-gulo-heptitol

Guidance literature:: With triethylsilane; boron trifluoride diethyl etherate; In acetonitrile; for 3h; Ambient temperature;
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

: 133191-81-8
2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-O-(trimethylacetyl)-D-glycero-D-gulo-heptitol

Guidance literature:: Multi-step reaction with 5 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

With pyridine; hydrogenchloride; triethylsilane; n-butyllithium; boron trifluoride diethyl etherate; hydrogenchloride; In tetrahydrofuran; acetonitrile;
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

: 133191-81-8
2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-O-(trimethylacetyl)-D-glycero-D-gulo-heptitol

Guidance literature:: Multi-step reaction with 4 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

With pyridine; hydrogenchloride; triethylsilane; boron trifluoride diethyl etherate; hydrogenchloride; In tetrahydrofuran; acetonitrile;
DOI:10.1021/jo00002a009