(1R)-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1-C-{3-[(ethyl)(2',3'-O-isopropylideneuridin-5'-yl)phosphono]-2-propen-1-yl}-1,4-imino-D-galactitol

Base Information

Chemical Name:(1R)-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1-C-{3-[(ethyl)(2',3'-O-isopropylideneuridin-5'-yl)phosphono]-2-propen-1-yl}-1,4-imino-D-galactitol
CAS No.:884507-81-7
Molecular Formula:C₅₉H₆₆N₃O₁₄P
Molecular Weight:1072.16
Hs Code.:

(1R)-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1-C-{3-[(ethyl)(2',3'-O-isopropylideneuridin-5'-yl)phosphono]-2-propen-1-yl}-1,4-imino-D-galactitol

Synonyms:(1R)-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1-C-{3-[(ethyl)(2',3'-O-isopropylideneuridin-5'-yl)phosphono]-2-propen-1-yl}-1,4-imino-D-galactitol

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Chemical Property of (1R)-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1-C-{3-[(ethyl)(2',3'-O-isopropylideneuridin-5'-yl)phosphono]-2-propen-1-yl}-1,4-imino-D-galactitol

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Technology Process of (1R)-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1-C-{3-[(ethyl)(2',3'-O-isopropylideneuridin-5'-yl)phosphono]-2-propen-1-yl}-1,4-imino-D-galactitol

There total 5 articles about (1R)-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1-C-{3-[(ethyl)(2',3'-O-isopropylideneuridin-5'-yl)phosphono]-2-propen-1-yl}-1,4-imino-D-galactitol 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: 61.0%

: 884507-80-6
ethyl (2',3'-O-isopropylideneuridin-5'-yl) vinylphosphonate

: 884507-72-6
1(R)-1-C-allyl-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-D-galactitol

: 884507-81-7
(1R)-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1-C-{3-[(ethyl)(2',3'-O-isopropylideneuridin-5'-yl)phosphono]-2-propen-1-yl}-1,4-imino-D-galactitol

: 884507-79-3
1,4-bis-[(1R)-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-D-galactitol-1-yl]-2-butene

Guidance literature:: [1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(O-isopropoxyphenylmethylene)ruthenium; In dichloromethane; at 40 ℃; for 44h;
DOI:10.1021/jo8001134

Reference yield: 51.0%

: 884507-80-6
ethyl (2',3'-O-isopropylideneuridin-5'-yl) vinylphosphonate

: 884507-72-6
1(R)-1-C-allyl-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-D-galactitol

: 884507-81-7
(1R)-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1-C-{3-[(ethyl)(2',3'-O-isopropylideneuridin-5'-yl)phosphono]-2-propen-1-yl}-1,4-imino-D-galactitol

Guidance literature:: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene](benzylidene)Ru(II) dichloride; In dichloromethane; at 40 ℃; for 44h;
DOI:10.1021/ol053078z

Reference yield:

: 1021325-68-7
N-benzyloxycarbonyl 2,3,5,6-tetra-O-benzyl-α,β-D-glucofuranosylamine

: 884507-81-7
(1R)-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1-C-{3-[(ethyl)(2',3'-O-isopropylideneuridin-5'-yl)phosphono]-2-propen-1-yl}-1,4-imino-D-galactitol

Guidance literature:: Multi-step reaction with 4 steps

1: 86 percent / Me₃SiOTf / acetonitrile / 82 h / -40 °C

2: 62 percent / Et₃N / CH₂Cl₂ / 5 h / 20 °C

3: t-BuOK / tetrahydrofuran / 12 h / 20 °C

4: 51 percent / Nolan catalyst / CH₂Cl₂ / 44 h / 40 °C

With trimethylsilyl trifluoromethanesulfonate; potassium tert-butylate; triethylamine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene](benzylidene)Ru(II) dichloride; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/ol053078z