(4-2H,4a-2H)-1-O-methoxymethyl-2,3,5-tri-O-benzyl-4a-carba-β-D-arabinofuranoside

Base Information

Chemical Name:(4-2H,4a-2H)-1-O-methoxymethyl-2,3,5-tri-O-benzyl-4a-carba-β-D-arabinofuranoside
CAS No.:392240-24-3
Molecular Formula:C₂₉H₃₄O₅
Molecular Weight:464.57
Hs Code.:

Synonyms:(4-2H,4a-2H)-1-O-methoxymethyl-2,3,5-tri-O-benzyl-4a-carba-β-D-arabinofuranoside

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Chemical Property of (4-2H,4a-2H)-1-O-methoxymethyl-2,3,5-tri-O-benzyl-4a-carba-β-D-arabinofuranoside

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Technology Process of (4-2H,4a-2H)-1-O-methoxymethyl-2,3,5-tri-O-benzyl-4a-carba-β-D-arabinofuranoside

There total 5 articles about (4-2H,4a-2H)-1-O-methoxymethyl-2,3,5-tri-O-benzyl-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: 82.0%

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

: 392240-24-3
(4-2H,4a-2H)-1-O-methoxymethyl-2,3,5-tri-O-benzyl-4a-carba-β-D-arabinofuranoside

Guidance literature:: With deuterium; Wilkinson's catalyst; In dichloromethane; at 20 ℃; for 6h;
DOI:10.1021/jo010827r

Reference yield:

: 19493-09-5
Methylenetriphenylphosphorane

: 392240-24-3
(4-2H,4a-2H)-1-O-methoxymethyl-2,3,5-tri-O-benzyl-4a-carba-β-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 5 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

5.1: 82 percent / D₂ / (Ph₃P)3RhCl / CH₂Cl₂ / 6 h / 20 °C

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

Reference yield:

: 257603-80-8
1,3,4-tri-O-benzyl-6,7-didehydro-6,7-dideoxy-5-O-methoxymethyl-L-arabino-hept-2-ulose

: 392240-24-3
(4-2H,4a-2H)-1-O-methoxymethyl-2,3,5-tri-O-benzyl-4a-carba-β-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 77 percent / tetrahydrofuran / 3 h / -78 - 20 °C

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

3: 82 percent / D₂ / (Ph₃P)3RhCl / CH₂Cl₂ / 6 h / 20 °C

With deuterium; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; Wilkinson's catalyst; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/jo010827r