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

Base Information

Chemical Name:(2S,3R,4R,5R)-2,3-bis(benzyloxy)-1-(dimethoxyphosphoryl)methyl-4-hydroxy cyclohex-1-ene-ethane-5,6-diol-O-isopropylidene
CAS No.:1597438-27-1
Molecular Formula:C₂₈H₃₇O₈P
Molecular Weight:532.571
Hs Code.:

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

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Chemical Property of (2S,3R,4R,5R)-2,3-bis(benzyloxy)-1-(dimethoxyphosphoryl)methyl-4-hydroxy cyclohex-1-ene-ethane-5,6-diol-O-isopropylidene

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Technology Process of (2S,3R,4R,5R)-2,3-bis(benzyloxy)-1-(dimethoxyphosphoryl)methyl-4-hydroxy cyclohex-1-ene-ethane-5,6-diol-O-isopropylidene

There total 2 articles about (2S,3R,4R,5R)-2,3-bis(benzyloxy)-1-(dimethoxyphosphoryl)methyl-4-hydroxy cyclohex-1-ene-ethane-5,6-diol-O-isopropylidene 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: 53.0%

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

: 121-45-9
phosphorous acid trimethyl ester

: 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

Guidance literature:: With zinc dibromide; at 25 - 100 ℃; for 2h; Inert atmosphere; Microwave irradiation;
DOI:10.1021/ol500848q

Reference yield:

: 2,3-di-O-benzyl-1,4’’,4’”-trideoxy-1-C-methylene-5,6-O-isopropylidene-1’-tri-Oisopropylsilyl-4-C-(prop-4’-enyl)-D-galacto-heptitol

: 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

Guidance literature:: Multi-step reaction with 3 steps

1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 6 h / 80 °C / Inert atmosphere

2: tetra-n-butylammoniumfluoride trihydrate / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

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

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetra-n-butylammoniumfluoride trihydrate; zinc dibromide; In tetrahydrofuran; toluene; 3: |Michaelis-Arbuzov Synthesis;
DOI:10.1021/ol500848q

Reference yield: 100.0%

: 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

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

Guidance literature:: (2S,3R,4R,5R)-2,3-bis(benzyloxy)-1-(dimethoxyphosphoryl)methyl-4-hydroxy cyclohex-1-ene-ethane-5,6-diol-O-isopropylidene; With trimethylsilyl bromide; In dichloromethane; at 20 ℃; for 2.5h; Inert atmosphere;

With hydrogen; palladium(II) hydroxide; In methanol; ethyl acetate; for 0.333333h; Inert atmosphere;
DOI:10.1021/ol500848q