(2R,3S,4R,4aS,5S,6S,8aS)-4,5,6-Tris-benzyloxy-2-[(1R,2R)-2-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl]-6-methyl-hexahydro-pyrano[2,3-b]pyran-3-ol

Base Information

Chemical Name:(2R,3S,4R,4aS,5S,6S,8aS)-4,5,6-Tris-benzyloxy-2-[(1R,2R)-2-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl]-6-methyl-hexahydro-pyrano[2,3-b]pyran-3-ol
CAS No.:123505-98-6
Molecular Formula:C₄₇H₆₂O₈Si
Molecular Weight:783.09
Hs Code.:

(2R,3S,4R,4aS,5S,6S,8aS)-4,5,6-Tris-benzyloxy-2-[(1R,2R)-2-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl]-6-methyl-hexahydro-pyrano[2,3-b]pyran-3-ol

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Chemical Property of (2R,3S,4R,4aS,5S,6S,8aS)-4,5,6-Tris-benzyloxy-2-[(1R,2R)-2-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl]-6-methyl-hexahydro-pyrano[2,3-b]pyran-3-ol

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Technology Process of (2R,3S,4R,4aS,5S,6S,8aS)-4,5,6-Tris-benzyloxy-2-[(1R,2R)-2-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl]-6-methyl-hexahydro-pyrano[2,3-b]pyran-3-ol

There total 2 articles about (2R,3S,4R,4aS,5S,6S,8aS)-4,5,6-Tris-benzyloxy-2-[(1R,2R)-2-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl]-6-methyl-hexahydro-pyrano[2,3-b]pyran-3-ol 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: 75.0%

: 128062-05-5
2,3,5,9-tetra-O-benzyl-4,8-dideoxy-4-C-(1'-formyl)-(1'S)-2,8-di-C-methyl-L-talo-L-altro-1',1-bipyranoside-decitol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 123505-98-6
(2R,3S,4R,4aS,5S,6S,8aS)-4,5,6-Tris-benzyloxy-2-[(1R,2R)-2-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl]-6-methyl-hexahydro-pyrano[2,3-b]pyran-3-ol

Guidance literature:: With 2,4-dimethylaminopyridine; triethylamine; In dichloromethane; for 16h; Ambient temperature;

Reference yield:

: (3S,4S,4aS,6R,7R,8S,8aR,9aS,10R,10aS)-3,4,6,10-Tetrakis-benzyloxy-7-(3,4-dimethyl-benzyloxy)-3,8-dimethyl-decahydro-1,5,9-trioxa-anthracene

: 123505-98-6
(2R,3S,4R,4aS,5S,6S,8aS)-4,5,6-Tris-benzyloxy-2-[(1R,2R)-2-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl]-6-methyl-hexahydro-pyrano[2,3-b]pyran-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 1) 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, H₂O, 2) NaBH₄ / 1) a) CH₂Cl₂, p-dioxane, r.t., 4h, b) 3,4-dimethoxybenzylalcohol 2) EtOH, r.t., 12h

2: 75 percent / triethylamin, 2,4-dimethylaminopyridine / CH₂Cl₂ / 16 h / Ambient temperature

With sodium tetrahydroborate; 2,4-dimethylaminopyridine; water; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane;

Reference yield:

: 123505-98-6
(2R,3S,4R,4aS,5S,6S,8aS)-4,5,6-Tris-benzyloxy-2-[(1R,2R)-2-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl]-6-methyl-hexahydro-pyrano[2,3-b]pyran-3-ol

: 128041-97-4
7,10-anhydro-2,3,5-tri-O-benzyl-11-bromo-4,6,8,11-tetradeoxy-4-C-(1'-formyl)-6-C-(1-methoxymethoxymethyl)-2,8,10-tri-C-methyl-D-(or L-)glycero-L-talo-L-altro-1',1-pyranose-undecitol

Guidance literature:: Multi-step reaction with 10 steps

1: 1) DMSO, oxalyl chloride / 1) CH₂Cl₂, -78 deg C, 2) a) 25 min, b) Et₃N

2: 95 percent / tetrahydrofuran / Ambient temperature

3: 54 percent / BH₃*THF / tetrahydrofuran / 7 h / 0 °C

4: 1) N,N-di-isopropylethylamine, 2) tetrabutylammonium fluoride / 1) CH₂Cl₂, r.t., 16h, 2)THF, r.t., 6h

5: 1) DMSO, oxalylchloride 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 20 min, 2) -78 to 0 deg C

6: tetrahydrofuran / -78 deg C to 0 deg C

7: 1) DMSO, oxalylchloride 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 20 min, 2) -78 to 0 deg C

8: tetrahydrofuran / 4 h / Ambient temperature

9: 94 percent / NBS, NaHCO₃ / acetonitrile / 0.17 h / 0 °C

10: 1) DMSO, oxalylchloride, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 20 min,

With N-Bromosuccinimide; borane-THF; oxalyl dichloride; Chloro-oxo-acetic acid; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; acetonitrile;