(2R,3R,4S,5R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-ethylsulfanyl-tetrahydro-pyran-3,4,5-triol

Base Information

Chemical Name:(2R,3R,4S,5R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-ethylsulfanyl-tetrahydro-pyran-3,4,5-triol
CAS No.:213767-36-3
Molecular Formula:C₂₄H₃₄O₅SSi
Molecular Weight:462.682
Hs Code.:

Synonyms:(2R,3R,4S,5R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-ethylsulfanyl-tetrahydro-pyran-3,4,5-triol

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Chemical Property of (2R,3R,4S,5R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-ethylsulfanyl-tetrahydro-pyran-3,4,5-triol

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Technology Process of (2R,3R,4S,5R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-ethylsulfanyl-tetrahydro-pyran-3,4,5-triol

There total 1 articles about (2R,3R,4S,5R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-ethylsulfanyl-tetrahydro-pyran-3,4,5-triol 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: 88.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 73494-52-7,686299-00-3
ethyl-(1-thio-α-D-galactopyranoside)

: 213767-36-3
(2R,3R,4S,5R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-ethylsulfanyl-tetrahydro-pyran-3,4,5-triol

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃;
DOI:10.1021/jo9806097

Reference yield: 74.0%

: 100-39-0
benzyl bromide

: 213767-36-3
(2R,3R,4S,5R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-ethylsulfanyl-tetrahydro-pyran-3,4,5-triol

: 213767-41-0
tert-Butyl-diphenyl-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; 1.) 0 deg C, 30 min, 2.) 0 deg C to room temperature, overnight;
DOI:10.1021/jo9806097

Reference yield:

: 213767-36-3
(2R,3R,4S,5R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-ethylsulfanyl-tetrahydro-pyran-3,4,5-triol

: 213768-21-9
methyl 2-O-(2',3',4'-tri-O-benzyl-α-D-galactopyranosyl)-4-O-benzyl-6,6'-di-O-(octane-1,8-diyl)-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 74 percent / NaH / dimethylformamide / 1.) 0 deg C, 30 min, 2.) 0 deg C to room temperature, overnight

2: 95 percent / TBAF / tetrahydrofuran / 6 h / Ambient temperature

3: 89 percent / pyridine / 8 h / 40 °C

4: 82 percent / NIS, triflic acid / CH₂Cl₂ / 0.5 h

5: 81 percent / p-toluenesulfonic acid / methanol; ethyl acetate / 7 h

6: 61 percent / NaH, Cs₂CO₃ / tetrahydrofuran / 24 h / Heating

7: 1.) t-BuOK, 2.) HgO, HgCl₂ / 1.) DMSO, 80 deg C, 2 h, 2.) acetone, H₂O, 30 min

With N-iodo-succinimide; trifluorormethanesulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hydride; caesium carbonate; toluene-4-sulfonic acid; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; pyridine; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo9806097