UDP-C-[(2S,3R,4R,5R)-cyclohex-1-ene-5,6-ethane-2,3,4,5,6-pentaol]phosphonate

Base Information

Chemical Name:UDP-C-[(2S,3R,4R,5R)-cyclohex-1-ene-5,6-ethane-2,3,4,5,6-pentaol]phosphonate
CAS No.:1597438-32-8
Molecular Formula:C₁₈H₂₈N₂O₁₆P₂
Molecular Weight:590.372
Hs Code.:

Synonyms:UDP-C-[(2S,3R,4R,5R)-cyclohex-1-ene-5,6-ethane-2,3,4,5,6-pentaol]phosphonate

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Chemical Property of UDP-C-[(2S,3R,4R,5R)-cyclohex-1-ene-5,6-ethane-2,3,4,5,6-pentaol]phosphonate

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Technology Process of UDP-C-[(2S,3R,4R,5R)-cyclohex-1-ene-5,6-ethane-2,3,4,5,6-pentaol]phosphonate

There total 4 articles about UDP-C-[(2S,3R,4R,5R)-cyclohex-1-ene-5,6-ethane-2,3,4,5,6-pentaol]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: 14.0%

: 1597438-28-2
C-[(2S,3R,4R,5R)-cyclohex-1-ene-5,6-ethane-2,3,4,5,6-pentaol]methylphosphonic acid

: 647032-50-6
UMP triethylammonium salt

: 1597438-32-8
UDP-C-[(2S,3R,4R,5R)-cyclohex-1-ene-5,6-ethane-2,3,4,5,6-pentaol]phosphonate

Guidance literature:: C-[(2S,3R,4R,5R)-cyclohex-1-ene-5,6-ethane-2,3,4,5,6-pentaol]methylphosphonic acid; In water; for 0.5h;

UMP triethylammonium salt; With N,N-dimethyl-aniline; triethylamine; In acetonitrile; at 0 ℃; for 0.583333h; Further stages; Molecular sieve; Inert atmosphere;
DOI:10.1021/ol500848q

Reference yield:

: 1597438-26-0
(2S,3R,4R,5R)-2,3-bis(benzyloxy)-4-hydroxycyclohex-1-ene-1-hydroxymethyl-ethane-5,6-diol-O-isopropylidene

: 1597438-32-8
UDP-C-[(2S,3R,4R,5R)-cyclohex-1-ene-5,6-ethane-2,3,4,5,6-pentaol]phosphonate

Guidance literature:: Multi-step reaction with 3 steps

1.1: zinc dibromide / 2 h / 25 - 100 °C / Inert atmosphere; Microwave irradiation

2.1: trimethylsilyl bromide / dichloromethane / 2.5 h / 20 °C / Inert atmosphere

2.2: 0.33 h / Inert atmosphere

3.1: Dowex 50WX₈-200 / water / 0.5 h

3.2: 0.58 h / 0 °C / Molecular sieve; Inert atmosphere

With trimethylsilyl bromide; zinc dibromide; In dichloromethane; water; 1.1: |Michaelis-Arbuzov Synthesis;
DOI:10.1021/ol500848q

Reference yield:

: 1597438-27-1
(2S,3R,4R,5R)-2,3-bis(benzyloxy)-1-(dimethoxyphosphoryl)methyl-4-hydroxy cyclohex-1-ene-ethane-5,6-diol-O-isopropylidene

: 1597438-32-8
UDP-C-[(2S,3R,4R,5R)-cyclohex-1-ene-5,6-ethane-2,3,4,5,6-pentaol]phosphonate

Guidance literature:: Multi-step reaction with 2 steps

1.1: trimethylsilyl bromide / dichloromethane / 2.5 h / 20 °C / Inert atmosphere

1.2: 0.33 h / Inert atmosphere

2.1: Dowex 50WX₈-200 / water / 0.5 h

2.2: 0.58 h / 0 °C / Molecular sieve; Inert atmosphere

With trimethylsilyl bromide; In dichloromethane; water;
DOI:10.1021/ol500848q