[(2S,3R,4S,5S,6S)-3,4-Bis-benzyloxy-5-iodo-6-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-(tert-butyl-dimethyl-silanyloxy)-acetaldehyde

Base Information

• Chemical Name: [(2S,3R,4S,5S,6S)-3,4-Bis-benzyloxy-5-iodo-6-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-(tert-butyl-dimethyl-silanyloxy)-acetaldehyde
• CAS No.: 137792-83-7
• Molecular Formula: C₃₅H₄₅IO₇Si
• Molecular Weight: 732.728

Synonyms:

Chemical Property of [(2S,3R,4S,5S,6S)-3,4-Bis-benzyloxy-5-iodo-6-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-(tert-butyl-dimethyl-silanyloxy)-acetaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2S,3R,4S,5S,6S)-3,4-Bis-benzyloxy-5-iodo-6-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-(tert-butyl-dimethyl-silanyloxy)-acetaldehyde

There total 10 articles about [(2S,3R,4S,5S,6S)-3,4-Bis-benzyloxy-5-iodo-6-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-(tert-butyl-dimethyl-silanyloxy)-acetaldehyde 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:

3-[(2S,3R,4S,5S,6S)-3,4-Bis-benzyloxy-5-iodo-6-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propane-1,2-diol → [(2S,3R,4S,5S,6S)-3,4-Bis-benzyloxy-5-iodo-6-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-(tert-butyl-dimethyl-silanyloxy)-acetaldehyde (137792-83-7,137792-84-8)

Guidance literature:

With lead(IV) acetate; sodium carbonate; In dichloromethane; at 0 ℃; for 0.25h; Yield given;

DOI:10.1021/jo00028a033

Reference yield:

(2R,3S,4R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol (87316-22-1) → [(2S,3R,4S,5S,6S)-3,4-Bis-benzyloxy-5-iodo-6-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-(tert-butyl-dimethyl-silanyloxy)-acetaldehyde (137792-83-7,137792-84-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 65 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 9 h / Ambient temperature

2: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature

3: pyridinium chlorochromate, 4-Angstroem molecular sieves / CH₂Cl₂

4: 73 percent / tetrahydrofuran / 1) -78 deg C, 30 min, 2) 0 deg C, 30 min

5: 92 percent / imidazole / dimethylformamide / Ambient temperature

6: 82 percent / N-iodosuccinimide / acetonitrile / 6 h / Ambient temperature

7: OsO₄, N-methylmorpholine oxide / acetone; 2-methyl-propan-2-ol; H₂O

8: Na₂CO₃, Pb(OAc)4 / CH₂Cl₂ / 0.25 h / 0 °C

With 1H-imidazole; lead(IV) acetate; N-iodo-succinimide; osmium(VIII) oxide; 4 A molecular sieve; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium carbonate; 4-methylmorpholine N-oxide; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol;

DOI:10.1021/jo00028a033

Reference yield:

benzyl bromide (100-39-0) → [(2S,3R,4S,5S,6S)-3,4-Bis-benzyloxy-5-iodo-6-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-(tert-butyl-dimethyl-silanyloxy)-acetaldehyde (137792-83-7,137792-84-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 65 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 9 h / Ambient temperature

2: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature

3: pyridinium chlorochromate, 4-Angstroem molecular sieves / CH₂Cl₂

4: 73 percent / tetrahydrofuran / 1) -78 deg C, 30 min, 2) 0 deg C, 30 min

5: 92 percent / imidazole / dimethylformamide / Ambient temperature

6: 82 percent / N-iodosuccinimide / acetonitrile / 6 h / Ambient temperature

7: OsO₄, N-methylmorpholine oxide / acetone; 2-methyl-propan-2-ol; H₂O

8: Na₂CO₃, Pb(OAc)4 / CH₂Cl₂ / 0.25 h / 0 °C

With 1H-imidazole; lead(IV) acetate; N-iodo-succinimide; osmium(VIII) oxide; 4 A molecular sieve; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium carbonate; 4-methylmorpholine N-oxide; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol;

DOI:10.1021/jo00028a033

upstream raw materials:

(2R,3S,4R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol

benzyl bromide

3,4-di-O-benzyl-D-glucal

(2S,3S,4R)-3,4-Bis-benzyloxy-3,4-dihydro-2H-pyran-2-carbaldehyde

Downstream raw materials:

[(1S,3S,4S,5R,6S,7S,8R)-7,8-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester

[(1S,3S,4S,5S,6S,7S,8R)-7,8-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester

[(1S,3S,4S,5R,6R,7S,8R)-7,8-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester

[(1S,3S,4S,5S,6R,7S,8R)-7,8-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester

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