(2R,3R,4S,5S,6R,1'R,2'S,4'S,2''R)-2-[1',2'-diacetoxy-5'-benzyloxy-4'-methoxy-pentyl]-4-triethylsilyloxy-6-[2''-hydroxy-3''-methoxypropyl]-2-methoxy-3,5-dimethyl-2,3,5,6-tetrahydro-4H-pyran

Base Information

Chemical Name:(2R,3R,4S,5S,6R,1'R,2'S,4'S,2''R)-2-[1',2'-diacetoxy-5'-benzyloxy-4'-methoxy-pentyl]-4-triethylsilyloxy-6-[2''-hydroxy-3''-methoxypropyl]-2-methoxy-3,5-dimethyl-2,3,5,6-tetrahydro-4H-pyran
CAS No.:795290-06-1
Molecular Formula:C₃₅H₆₀O₁₁Si
Molecular Weight:684.94
Hs Code.:

(2R,3R,4S,5S,6R,1'R,2'S,4'S,2''R)-2-[1',2'-diacetoxy-5'-benzyloxy-4'-methoxy-pentyl]-4-triethylsilyloxy-6-[2''-hydroxy-3''-methoxypropyl]-2-methoxy-3,5-dimethyl-2,3,5,6-tetrahydro-4H-pyran

Synonyms:(2R,3R,4S,5S,6R,1'R,2'S,4'S,2''R)-2-[1',2'-diacetoxy-5'-benzyloxy-4'-methoxy-pentyl]-4-triethylsilyloxy-6-[2''-hydroxy-3''-methoxypropyl]-2-methoxy-3,5-dimethyl-2,3,5,6-tetrahydro-4H-pyran

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Chemical Property of (2R,3R,4S,5S,6R,1'R,2'S,4'S,2''R)-2-[1',2'-diacetoxy-5'-benzyloxy-4'-methoxy-pentyl]-4-triethylsilyloxy-6-[2''-hydroxy-3''-methoxypropyl]-2-methoxy-3,5-dimethyl-2,3,5,6-tetrahydro-4H-pyran

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Technology Process of (2R,3R,4S,5S,6R,1'R,2'S,4'S,2''R)-2-[1',2'-diacetoxy-5'-benzyloxy-4'-methoxy-pentyl]-4-triethylsilyloxy-6-[2''-hydroxy-3''-methoxypropyl]-2-methoxy-3,5-dimethyl-2,3,5,6-tetrahydro-4H-pyran

There total 11 articles about (2R,3R,4S,5S,6R,1'R,2'S,4'S,2''R)-2-[1',2'-diacetoxy-5'-benzyloxy-4'-methoxy-pentyl]-4-triethylsilyloxy-6-[2''-hydroxy-3''-methoxypropyl]-2-methoxy-3,5-dimethyl-2,3,5,6-tetrahydro-4H-pyran 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%

: Acetic acid (1R,2S,4S)-2-acetoxy-5-benzyloxy-4-methoxy-1-[(2R,3R,4S,5S,6R)-2-methoxy-6-((R)-3-methoxy-2-triethylsilanyloxy-propyl)-3,5-dimethyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl]-pentyl ester

: 795290-06-1
(2R,3R,4S,5S,6R,1'R,2'S,4'S,2''R)-2-[1',2'-diacetoxy-5'-benzyloxy-4'-methoxy-pentyl]-4-triethylsilyloxy-6-[2''-hydroxy-3''-methoxypropyl]-2-methoxy-3,5-dimethyl-2,3,5,6-tetrahydro-4H-pyran

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃;
DOI:10.1002/anie.200460172

Reference yield:

: 945534-62-3
(2R,3R,4S,5S,6R,1'R,2'S,4'S)-2-[1',2'-diacetoxy-5'-benzyloxy-4'-methoxy-pentyl]-4-triethylsilyloxy-6-allyl-2-methoxy-3,5-dimethyl-2,3,5,6-tetrahydro-4H-pyran

: 795290-06-1
(2R,3R,4S,5S,6R,1'R,2'S,4'S,2''R)-2-[1',2'-diacetoxy-5'-benzyloxy-4'-methoxy-pentyl]-4-triethylsilyloxy-6-[2''-hydroxy-3''-methoxypropyl]-2-methoxy-3,5-dimethyl-2,3,5,6-tetrahydro-4H-pyran

Guidance literature:: Multi-step reaction with 2 steps

1: (DHQD)2PYR; K₃Fe(CN)6; K₂CO₃ / K₂OsO₄*2H₂O / 2-methyl-propan-2-ol; H₂O / 6 h / 0 °C

2: 177 mg / Ag₂O / dimethylformamide / 20 h / 20 °C

With hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; potassium carbonate; silver(l) oxide; potassium hexacyanoferrate(III); potassium osmate(VI); In water; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Sharpless dihydroxylation;
DOI:10.1039/b701293d

Reference yield:

: (4S,5S,6E)-3,5-dimethyl-4-((1'R)-1'-phenylethoxy)oct-6-en-2-one

: 795290-06-1
(2R,3R,4S,5S,6R,1'R,2'S,4'S,2''R)-2-[1',2'-diacetoxy-5'-benzyloxy-4'-methoxy-pentyl]-4-triethylsilyloxy-6-[2''-hydroxy-3''-methoxypropyl]-2-methoxy-3,5-dimethyl-2,3,5,6-tetrahydro-4H-pyran

Guidance literature:: Multi-step reaction with 9 steps

1.1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

1.2: 75 percent / mCPBA / CH₂Cl₂ / 1 h / 0 °C

2.1: sodium bis(trimethylsilyl)amide; TMSCl / tetrahydrofuran / 2 h / -78 - 20 °C

2.2: 73 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / -78 °C

3.1: NaHCO₃; ozone / CH₂Cl₂ / -78 °C

3.2: Me₂S / CH₂Cl₂ / 1 h / -78 - 20 °C

4.1: (+)-B-methoxydiisopinocampheylborane; ozone / diethyl ether; pentane / 3 h / 20 °C

4.2: diethyl ether; pentane / 1 h / -78 °C

4.3: 3.1 g / NaBO₃*4H₂O / tetrahydrofuran; H₂O / 12 h / 20 °C

5.1: HCl / 3 h / 50 °C

6.1: 810 mg / pyridine / 3 h / 0 - 20 °C

7.1: 92 percent / imidazole / CH₂Cl₂ / 2 h / 20 °C

8.1: (DHQD)2PYR; K₃Fe(CN)6; K₂CO₃ / K₂OsO₄*2H₂O / 2-methyl-propan-2-ol; H₂O / 6 h / 0 °C

9.1: 177 mg / Ag₂O / dimethylformamide / 20 h / 20 °C

With (+)-Ipc₂BOMe; 1H-imidazole; hydrogenchloride; chloro-trimethyl-silane; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; sodium hexamethyldisilazane; sodium hydrogencarbonate; potassium carbonate; ozone; triethylamine; silver(l) oxide; potassium hexacyanoferrate(III); potassium osmate(VI); In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; pentane; 1.2: Rubottom oxidation / 8.1: Sharpless dihydroxylation;
DOI:10.1039/b701293d