1-[(2S,3R,4R,5S,6R)-6-((1R,2R)-1-Benzyloxy-2-hydroxy-propyl)-5-methyl-3,4-bis-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-yl]-propan-2-one

Base Information

Chemical Name:1-[(2S,3R,4R,5S,6R)-6-((1R,2R)-1-Benzyloxy-2-hydroxy-propyl)-5-methyl-3,4-bis-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-yl]-propan-2-one
CAS No.:194934-62-8
Molecular Formula:C₃₁H₅₆O₈Si₂
Molecular Weight:612.952
Hs Code.:

1-[(2S,3R,4R,5S,6R)-6-((1R,2R)-1-Benzyloxy-2-hydroxy-propyl)-5-methyl-3,4-bis-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-yl]-propan-2-one

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Chemical Property of 1-[(2S,3R,4R,5S,6R)-6-((1R,2R)-1-Benzyloxy-2-hydroxy-propyl)-5-methyl-3,4-bis-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-yl]-propan-2-one

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Technology Process of 1-[(2S,3R,4R,5S,6R)-6-((1R,2R)-1-Benzyloxy-2-hydroxy-propyl)-5-methyl-3,4-bis-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-yl]-propan-2-one

There total 11 articles about 1-[(2S,3R,4R,5S,6R)-6-((1R,2R)-1-Benzyloxy-2-hydroxy-propyl)-5-methyl-3,4-bis-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-yl]-propan-2-one 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:

: 194934-61-7
(E)-(5R,6R,7R)-7-((4R,5R,6R)-5-Benzyloxy-2,2,6-trimethyl-[1,3]dioxan-4-yl)-5,6-bis-(2-trimethylsilanyl-ethoxymethoxy)-oct-3-en-2-one

: 194934-62-8
1-[(2S,3R,4R,5S,6R)-6-((1R,2R)-1-Benzyloxy-2-hydroxy-propyl)-5-methyl-3,4-bis-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-yl]-propan-2-one

Guidance literature:: With acetic acid; In tetrahydrofuran; water; at 20 ℃; for 19h; Yield given;
DOI:10.1016/S0040-4039(97)01257-4

Reference yield:

: 194934-61-7
(E)-(5R,6R,7R)-7-((4R,5R,6R)-5-Benzyloxy-2,2,6-trimethyl-[1,3]dioxan-4-yl)-5,6-bis-(2-trimethylsilanyl-ethoxymethoxy)-oct-3-en-2-one

: 194934-62-8
1-[(2S,3R,4R,5S,6R)-6-((1R,2R)-1-Benzyloxy-2-hydroxy-propyl)-5-methyl-3,4-bis-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-yl]-propan-2-one

: 1-[(2R,3R,4R,5S,6R)-6-((1R,2R)-1-Benzyloxy-2-hydroxy-propyl)-5-methyl-3,4-bis-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-yl]-propan-2-one

Guidance literature:: With acetic acid; In tetrahydrofuran; water; at 20 ℃; for 19h; Yield given. Yields of byproduct given;
DOI:10.1016/S0040-4039(97)01257-4

Reference yield:

: 194934-58-2
(S)-2-[5-(R)-benzyloxy-2,2,6-(6R)-trimethyl-1,3-dioxan-4-(R)-yl]-propionaldehyde

: 194934-62-8
1-[(2S,3R,4R,5S,6R)-6-((1R,2R)-1-Benzyloxy-2-hydroxy-propyl)-5-methyl-3,4-bis-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-yl]-propan-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 88 percent / i-Pr₂NEt, LiCl / acetonitrile / 17 h / 20 °C

2: 98 percent / AD-mix-β<(DHQD)2PHAL>, K2OsO2(OH)4, K3Fe(CN)6, K2CO3, MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 17 h / 20 °C

3: 97 percent / i-Pr₂Et, CH₂Cl₂ / CH₂Cl₂ / 24 h / 40 °C

4: DIBAL / CH₂Cl₂ / 1 h / -100 °C

5: Ba(OH)2*2H₂O / tetrahydrofuran; H₂O / 22 h / 20 °C

6: AcOH / tetrahydrofuran; H₂O / 19 h / 20 °C

With barium dihydroxide; potassium dioxotetrahydroxoosmate(VI); dichloromethane; methanesulfonamide; i-Pr₂Et; diisobutylaluminium hydride; potassium carbonate; acetic acid; 1,4-bis(9-O-dihydroquinidine)phthalazine; N-ethyl-N,N-diisopropylamine; lithium chloride; potassium hexacyanoferrate(III); In tetrahydrofuran; dichloromethane; water; acetonitrile; tert-butyl alcohol;
DOI:10.1016/S0040-4039(97)01257-4