2,3,5-tri-O-benzyl-4-dehydro-4-deoxy-1-O-methoxymethyl-4a-carba-β-D-arabinofuranoside

Base Information

Chemical Name:2,3,5-tri-O-benzyl-4-dehydro-4-deoxy-1-O-methoxymethyl-4a-carba-β-D-arabinofuranoside
CAS No.:257603-82-0
Molecular Formula:C₂₉H₃₂O₅
Molecular Weight:460.57
Hs Code.:

Synonyms:2,3,5-tri-O-benzyl-4-dehydro-4-deoxy-1-O-methoxymethyl-4a-carba-β-D-arabinofuranoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 2,3,5-tri-O-benzyl-4-dehydro-4-deoxy-1-O-methoxymethyl-4a-carba-β-D-arabinofuranoside

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of 2,3,5-tri-O-benzyl-4-dehydro-4-deoxy-1-O-methoxymethyl-4a-carba-β-D-arabinofuranoside

There total 4 articles about 2,3,5-tri-O-benzyl-4-dehydro-4-deoxy-1-O-methoxymethyl-4a-carba-β-D-arabinofuranoside 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: 78.0%

: 257603-81-9
4,5,7-tri-O-benzyl-1,2-didehydro-1,2,6-trideoxy-3-O-methoxymethyl-6-C-methylene-D-arabino-heptitol

: 257603-82-0
2,3,5-tri-O-benzyl-4-dehydro-4-deoxy-1-O-methoxymethyl-4a-carba-β-D-arabinofuranoside

Guidance literature:: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In toluene; at 60 ℃; for 2.5h;
DOI:10.1021/jo010827r

Reference yield:

: 257603-79-5
4,5,7-tri-O-benzyl-1,2-didehydro-1,2-dideoxy-3-O-methoxymethyl-D-manno-heptitol

: 257603-82-0
2,3,5-tri-O-benzyl-4-dehydro-4-deoxy-1-O-methoxymethyl-4a-carba-β-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 93 percent / PCC; NaOAc; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 20 °C

2: 77 percent / tetrahydrofuran / 3 h / -78 - 20 °C

3: 78 percent / (1,3-Mes-imidazolidin-2-yl)-(PhC=)RuCl₂PCy₃ / toluene / 2.5 h / 60 °C

With 4 A molecular sieve; sodium acetate; pyridinium chlorochromate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/jo010827r

Reference yield:

: 19493-09-5
Methylenetriphenylphosphorane

: 257603-82-0
2,3,5-tri-O-benzyl-4-dehydro-4-deoxy-1-O-methoxymethyl-4a-carba-β-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-BuLi / tetrahydrofuran / 0.17 h / 0 °C

1.2: 78 percent / tetrahydrofuran / 10 h / -78 - 20 °C

2.1: 93 percent / PCC; NaOAc; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 20 °C

3.1: 77 percent / tetrahydrofuran / 3 h / -78 - 20 °C

4.1: 78 percent / (1,3-Mes-imidazolidin-2-yl)-(PhC=)RuCl₂PCy₃ / toluene / 2.5 h / 60 °C

With n-butyllithium; 4 A molecular sieve; sodium acetate; pyridinium chlorochromate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/jo010827r