(2S,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde

Base Information

• Chemical Name: (2S,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde
• CAS No.: 193223-12-0
• Molecular Formula: C₂₉H₅₀O₇Si₂
• Molecular Weight: 566.883

Synonyms:(2S,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde

Chemical Property of (2S,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde

There total 6 articles about (2S,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde 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:

[(2R,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-methanol (193222-97-8) → (2S,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde (193223-12-0) + (2S,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid (193223-08-4)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; sodium chloride; potassium bromide; In dichloromethane; at 20 ℃; for 3.5h;

DOI:10.1002/prac.19973390162

Reference yield:

allyl β-D-glucopyranoside (2595-07-5,7464-56-4,34384-79-7,41308-76-3,48149-72-0,48149-74-2,85249-43-0,119479-69-5,821794-45-0) → (2S,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde (193223-12-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / p-TsOH*H₂O / dimethylformamide / 4 h / 40 °C / 75.01 Torr

2: 99 percent / imidazole / dimethylformamide / 72 h / 40 °C

3: 97 percent / molecuar sieves 3 Angstroem, NaCNBH₃, Me₃SiCl / acetonitrile / 28.5 h / 20 °C

4: TEMPO, Bu₄NCl, KBr, sat. aq. NaCl, sat. aq. NaHCO₃, aq. NaClO / CH₂Cl₂ / 3.5 h / 20 °C

With 1H-imidazole; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; chloro-trimethyl-silane; tetrabutyl-ammonium chloride; sodium cyanoborohydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; sodium chloride; potassium bromide; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/prac.19973390162

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → (2S,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde (193223-12-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / p-TsOH*H₂O / dimethylformamide / 4 h / 40 °C / 75.01 Torr

2: 99 percent / imidazole / dimethylformamide / 72 h / 40 °C

3: 97 percent / molecuar sieves 3 Angstroem, NaCNBH₃, Me₃SiCl / acetonitrile / 28.5 h / 20 °C

4: TEMPO, Bu₄NCl, KBr, sat. aq. NaCl, sat. aq. NaHCO₃, aq. NaClO / CH₂Cl₂ / 3.5 h / 20 °C

With 1H-imidazole; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; chloro-trimethyl-silane; tetrabutyl-ammonium chloride; sodium cyanoborohydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; sodium chloride; potassium bromide; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/prac.19973390162

upstream raw materials:

[(2R,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-methanol

allyl β-D-glucopyranoside

p-Anisaldehyde dimethyl acetal

allyl 4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside

Downstream raw materials:

(2S,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid

(2S,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid amide

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