(2S,4R,4'S,6'R)-1-[6'-benzyloxymethyl-4'-(4-methoxy-benzyloxy)-5',6'-dihydro-4'H-pyran-2'-yl]-6-(4-methoxy-benzyloxy)-hexane-2,4-diol

Base Information

Chemical Name:(2S,4R,4'S,6'R)-1-[6'-benzyloxymethyl-4'-(4-methoxy-benzyloxy)-5',6'-dihydro-4'H-pyran-2'-yl]-6-(4-methoxy-benzyloxy)-hexane-2,4-diol
CAS No.:474745-86-3
Molecular Formula:C₃₅H₄₄O₈
Molecular Weight:592.73
Hs Code.:

Synonyms:(2S,4R,4'S,6'R)-1-[6'-benzyloxymethyl-4'-(4-methoxy-benzyloxy)-5',6'-dihydro-4'H-pyran-2'-yl]-6-(4-methoxy-benzyloxy)-hexane-2,4-diol

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Chemical Property of (2S,4R,4'S,6'R)-1-[6'-benzyloxymethyl-4'-(4-methoxy-benzyloxy)-5',6'-dihydro-4'H-pyran-2'-yl]-6-(4-methoxy-benzyloxy)-hexane-2,4-diol

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Technology Process of (2S,4R,4'S,6'R)-1-[6'-benzyloxymethyl-4'-(4-methoxy-benzyloxy)-5',6'-dihydro-4'H-pyran-2'-yl]-6-(4-methoxy-benzyloxy)-hexane-2,4-diol

There total 14 articles about (2S,4R,4'S,6'R)-1-[6'-benzyloxymethyl-4'-(4-methoxy-benzyloxy)-5',6'-dihydro-4'H-pyran-2'-yl]-6-(4-methoxy-benzyloxy)-hexane-2,4-diol 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: 90.0%

: 474745-97-6
(2R,4S,2'S,4'R)-2-benzyloxymethyl-6-[2',4'-bis(tert-butyldimethylsilanyloxy)-6'-(4-methoxy-benzyloxy)-hexyl]-4-(4-methoxy-benzyloxy)-3,4-dihydro-2H-pyran

: 474745-86-3
(2S,4R,4'S,6'R)-1-[6'-benzyloxymethyl-4'-(4-methoxy-benzyloxy)-5',6'-dihydro-4'H-pyran-2'-yl]-6-(4-methoxy-benzyloxy)-hexane-2,4-diol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 23 ℃; for 12h;
DOI:10.1021/ol0266875

Reference yield:

: (3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-7-[(4-methoxy-benzyl)oxy]-heptanal

: 474745-86-3
(2S,4R,4'S,6'R)-1-[6'-benzyloxymethyl-4'-(4-methoxy-benzyloxy)-5',6'-dihydro-4'H-pyran-2'-yl]-6-(4-methoxy-benzyloxy)-hexane-2,4-diol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 91 percent / 2,2-dimethyl-2-butene; NaH₂PO₄; NaClO₂ / H₂O; tetrahydrofuran / 2 h / 23 °C

2.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / CH₂Cl₂ / 3 h / 23 °C

2.2: 98 percent / DMAP / CH₂Cl₂ / 4 h / 23 °C

3.1: 75 percent / pyridine / tetrahydrofuran; toluene / 0 - 23 °C

4.1: 81 percent / Grubbs's second generation catalyst / benzene / 4 h / 45 °C

5.1: 90 percent / TBAF / tetrahydrofuran / 12 h / 23 °C

With pyridine; sodium chlorite; sodium dihydrogenphosphate; 2,2-dimethyl-2-butene; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; triethylamine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; water; toluene; benzene; 3.1: Tebbe olefination;
DOI:10.1021/ol0266875

Reference yield:

: 118207-58-2
5-(4-methoxybenzyloxy)-3-oxopentanoic acid methyl ester

: 474745-86-3
(2S,4R,4'S,6'R)-1-[6'-benzyloxymethyl-4'-(4-methoxy-benzyloxy)-5',6'-dihydro-4'H-pyran-2'-yl]-6-(4-methoxy-benzyloxy)-hexane-2,4-diol

Guidance literature:: Multi-step reaction with 10 steps

1.1: H₂ / (R)-BINAP-Ru(II)Cl₂ / methanol / 72 h / 23 °C / 76005.1 Torr

2.1: nBuLi; diisopropylamine / tetrahydrofuran; hexane / 1 h / -40 °C

2.2: 85 percent / tetrahydrofuran; hexane / 1 h / -40 °C

3.1: 86 percent / tetramethylammonium triacetoxyborohydride / acetic acid; acetonitrile / 48 h / -30 °C

4.1: 77 percent / Et₃N; DMAP / CH₂Cl₂ / 18 h / 23 °C

5.1: 94 percent / DIBAL / CH₂Cl₂; hexane / 2 h / -78 °C

6.1: 91 percent / 2,2-dimethyl-2-butene; NaH₂PO₄; NaClO₂ / H₂O; tetrahydrofuran / 2 h / 23 °C

7.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / CH₂Cl₂ / 3 h / 23 °C

7.2: 98 percent / DMAP / CH₂Cl₂ / 4 h / 23 °C

8.1: 75 percent / pyridine / tetrahydrofuran; toluene / 0 - 23 °C

9.1: 81 percent / Grubbs's second generation catalyst / benzene / 4 h / 45 °C

10.1: 90 percent / TBAF / tetrahydrofuran / 12 h / 23 °C

With pyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2,2-dimethyl-2-butene; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; triethylamine; diisopropylamine; tetramethylammonium triacetoxyborohydride; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; RuCl₂[(R)-BINAP]; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetic acid; toluene; acetonitrile; benzene; 1.1: Noyori hydrogenaion / 8.1: Tebbe olefination;
DOI:10.1021/ol0266875