(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-[(dimethyl-phenyl-silanyl)-methyl]-6-methoxy-tetrahydro-pyran-3-ol

Base Information

Chemical Name:(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-[(dimethyl-phenyl-silanyl)-methyl]-6-methoxy-tetrahydro-pyran-3-ol
CAS No.:444600-30-0
Molecular Formula:C₂₉H₃₆O₅Si
Molecular Weight:492.687
Hs Code.:

Synonyms:(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-[(dimethyl-phenyl-silanyl)-methyl]-6-methoxy-tetrahydro-pyran-3-ol

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Chemical Property of (2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-[(dimethyl-phenyl-silanyl)-methyl]-6-methoxy-tetrahydro-pyran-3-ol

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Technology Process of (2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-[(dimethyl-phenyl-silanyl)-methyl]-6-methoxy-tetrahydro-pyran-3-ol

There total 2 articles about (2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-[(dimethyl-phenyl-silanyl)-methyl]-6-methoxy-tetrahydro-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:

: 107735-20-6
[(dimethylphenylsilyl)methyl]magnesium chloride

: (3S,4R,5R)-4,5-Bis-benzyloxy-3-methoxy-2,7-dioxa-bicyclo[4.1.0]heptane

: 444600-30-0
(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-[(dimethyl-phenyl-silanyl)-methyl]-6-methoxy-tetrahydro-pyran-3-ol

: (2S,3S,4S,5R,6S)-4,5-Bis-benzyloxy-2-[(dimethyl-phenyl-silanyl)-methyl]-6-methoxy-tetrahydro-pyran-3-ol

Guidance literature:: With copper(l) iodide; In tetrahydrofuran; at -10 ℃; for 0.333333h;
DOI:10.1021/ol026175q

Reference yield:

: 50711-27-8
methyl 2,3-di-O-benzyl-4-deoxy-β-L-threo-pent-4-enopyranoside

: 444600-30-0
(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-[(dimethyl-phenyl-silanyl)-methyl]-6-methoxy-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 99 percent / 2,2-dimethyldioxirane / acetone; CH₂Cl₂ / 48 h / -55 °C

2: copper(I) iodide / tetrahydrofuran / 0.33 h / -10 °C

With copper(l) iodide; 2,2-dimethyldioxirane; In tetrahydrofuran; dichloromethane; acetone; 2: Grignard addition;
DOI:10.1021/ol026175q

Reference yield:

: 444600-30-0
(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-[(dimethyl-phenyl-silanyl)-methyl]-6-methoxy-tetrahydro-pyran-3-ol

: 50711-27-8
methyl 2,3-di-O-benzyl-4-deoxy-β-L-threo-pent-4-enopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: peracetic acid; potassium bromide; sodium acetate / acetic acid / 20 h / 0 - 20 °C

2.1: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; sodium hypochlorite; sodium hydrogen carbonate / tetra-n-butylammonium bromide; potassium bromide / CH₂Cl₂; H₂O / 0.75 h / 0 °C

2.2: 70 percent / N,N-dimethylformamide dineopentyl acetal / toluene / 1 h / 120 °C

With peracetic acid; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium acetate; sodium hydrogencarbonate; potassium bromide; tetrabutylammomium bromide; potassium bromide; In dichloromethane; water; acetic acid; 1.1: Tamao-Fleming oxidation;
DOI:10.1021/ol026175q