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

Base Information

Chemical Name:diethyl (((2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate
CAS No.:92619-96-0
Molecular Formula:C₃₉H₄₇O₈P
Molecular Weight:674.771
Hs Code.:

Synonyms:diethyl (((2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate

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Chemical Property of diethyl (((2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate

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Technology Process of diethyl (((2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate

There total 7 articles about diethyl (((2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate 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: 84.0%

: 92517-03-8
(2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(iodomethyl)tetrahydro-2H-pyran

: 122-52-1
triethyl phosphite

: 92619-96-0
diethyl (((2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate

Guidance literature:: for 3h; Heating;
DOI:10.1016/0008-6215(84)85416-6

Reference yield:

: 100-39-0
benzyl bromide

: 92619-96-0
diethyl (((2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

1.2: 16 h / 20 °C / Inert atmosphere

2.1: acetic acid; sulfuric acid / water / 10 h / 0 - 80 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

3.2: 18 h / -78 - 20 °C / Inert atmosphere

4.1: mercury(II) diacetate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

4.2: 0.5 h

5.1: iodine / dichloromethane / 16 h / 20 °C

6.1: 16 h / 160 °C / Sealed tube

With n-butyllithium; sulfuric acid; mercury(II) diacetate; iodine; sodium hydride; acetic acid; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

: 3879-79-6,17791-37-6,19488-61-0,53008-63-2,69237-94-1,69237-95-2,71526-33-5,83462-67-3,84799-77-9,103421-29-0,103421-30-3,139241-42-2,61330-62-9
(2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran

: 92619-96-0
diethyl (((2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate

Guidance literature:: Multi-step reaction with 5 steps

1.1: acetic acid; sulfuric acid / water / 10 h / 0 - 80 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

2.2: 18 h / -78 - 20 °C / Inert atmosphere

3.1: mercury(II) diacetate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

3.2: 0.5 h

4.1: iodine / dichloromethane / 16 h / 20 °C

5.1: 16 h / 160 °C / Sealed tube

With n-butyllithium; sulfuric acid; mercury(II) diacetate; iodine; acetic acid; In tetrahydrofuran; hexane; dichloromethane; water;