methyl 3-O-[tert-butyl-(diphenyl)silyl]-2,4-dideoxy-D-threo-hexopyranoside

Base Information

• Chemical Name: methyl 3-O-[tert-butyl-(diphenyl)silyl]-2,4-dideoxy-D-threo-hexopyranoside
• CAS No.: 530112-01-7
• Molecular Formula: C₂₃H₃₂O₄Si
• Molecular Weight: 400.59
• Mol file: 530112-01-7.mol

Synonyms:methyl 3-O-[tert-butyl-(diphenyl)silyl]-2,4-dideoxy-D-threo-hexopyranoside

Chemical Property of methyl 3-O-[tert-butyl-(diphenyl)silyl]-2,4-dideoxy-D-threo-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-O-[tert-butyl-(diphenyl)silyl]-2,4-dideoxy-D-threo-hexopyranoside

There total 1 articles about methyl 3-O-[tert-butyl-(diphenyl)silyl]-2,4-dideoxy-D-threo-hexopyranoside 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: 65.0%

methanol (67-56-1) + 2,6-anhydro-1-O-[tert-butyl(dimethyl)silyl]-4-O-[tert-butyl-(diphenyl)silyl]-3,5-dideoxy-D-threo-hex-5-enitol (529488-03-7) → methyl 3-O-[tert-butyl-(diphenyl)silyl]-2,4-dideoxy-D-threo-hexopyranoside (530112-01-7)

Guidance literature:

With triphenylphosphine hydrobromide; In dichloromethane; at 0 - 20 ℃; for 5h;

DOI:10.1039/b209637b

Reference yield: 96.0%

trifluoromethylsulfonic anhydride (358-23-6) + methyl 3-O-[tert-butyl-(diphenyl)silyl]-2,4-dideoxy-D-threo-hexopyranoside (530112-01-7) → Trifluoro-methanesulfonic acid (2S,4S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester (529488-04-8)

Guidance literature:

With pyridine; In dichloromethane; at -12 ℃; for 0.25h;

DOI:10.1039/b209637b

Reference yield:

methyl 3-O-[tert-butyl-(diphenyl)silyl]-2,4-dideoxy-D-threo-hexopyranoside (530112-01-7) → 2-[(2R,4S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl]-6-hydroxy-benzoic acid

Guidance literature:

Multi-step reaction with 5 steps

1.1: 96 percent / pyridine / CH₂Cl₂ / 0.25 h / -12 °C

2.1: Mg; I₂ / tetrahydrofuran / 1 h / 20 °C

2.2: 59 percent / CuBr / tetrahydrofuran / 14 h / 0 °C

3.1: O₃/O₂ / CH₂Cl₂ / 0.5 h / -78 °C

3.2: 68 percent / PPh₃; O₂ / CH₂Cl₂ / 4 h / -78 - 20 °C

4.1: 94 percent / NaClO₂; NaHSO₃; aq. H₂O₂ / NaH₂PO₄ / acetonitrile / 3.5 h / 20 °C

5.1: K₂CO₃ / methanol / 1 h / 20 °C

With pyridine; sodium chlorite; dihydrogen peroxide; iodine; oxygen; potassium carbonate; ozone; sodium hydrogensulfite; magnesium; sodium dihydrogenphosphate; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1039/b209637b

upstream raw materials:

methanol

2,6-anhydro-1-O-[tert-butyl(dimethyl)silyl]-4-O-[tert-butyl-(diphenyl)silyl]-3,5-dideoxy-D-threo-hex-5-enitol

Downstream raw materials:

Trifluoro-methanesulfonic acid (2S,4S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

{(4S,6R)-2-methoxy-6-[(2-methyl-1-benzofuran-4-yl)methyl]-tetrahydro-2H-pyran-4-yloxy}(tert-butyl)diphenylsilane

3-{(2R,4S)-4-[tert-butyl(diphenyl)silyloxy]-6-methoxytetrahydro-2H-pyran-2-ylmethyl}-2-formylphenyl acetate

{(2S,4S,6R)-2-allyl-6-[(2-methyl-1-benzofuran-4-yl)methyl]-tetrahydro-2H-pyran-4-yloxy}(tert-butyl)diphenylsilane