methyl 3-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,4-bis-O-(methylsulfanylthiocarbonyl)-α-D-galactopyranoside

Base Information

• Chemical Name: methyl 3-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,4-bis-O-(methylsulfanylthiocarbonyl)-α-D-galactopyranoside
• CAS No.: 614752-11-3
• Molecular Formula: C₂₄H₃₈O₆S₄Si
• Molecular Weight: 578.912
• Mol file: 614752-11-3.mol

Synonyms:methyl 3-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,4-bis-O-(methylsulfanylthiocarbonyl)-α-D-galactopyranoside

Chemical Property of methyl 3-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,4-bis-O-(methylsulfanylthiocarbonyl)-α-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,4-bis-O-(methylsulfanylthiocarbonyl)-α-D-galactopyranoside

There total 3 articles about methyl 3-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,4-bis-O-(methylsulfanylthiocarbonyl)-α-D-galactopyranoside 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: 90.0%

carbon disulfide (75-15-0,12122-00-8) + methyl-6-(tert-butyldimethylsilyloxy)-3-O-benzyl-α-D-galactopyranoside (614752-07-7) + methyl iodide (74-88-4) → methyl 3-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,4-bis-O-(methylsulfanylthiocarbonyl)-α-D-galactopyranoside (614752-11-3)

Guidance literature:

carbon disulfide; methyl-6-(tert-butyldimethylsilyloxy)-3-O-benzyl-α-D-galactopyranoside; With 1H-imidazole; sodium hydride; In tetrahydrofuran; at 20 ℃; for 7h;

methyl iodide; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1016/S0040-4020(03)01103-7

Reference yield:

benzyl bromide (100-39-0) → methyl 3-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,4-bis-O-(methylsulfanylthiocarbonyl)-α-D-galactopyranoside (614752-11-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Bu₂SnO / benzene / 16 h / Heating

1.2: 49 percent / n-Bu₄NI / benzene / 4 h / Heating

2.1: 87 percent / imidazole / dimethylformamide / 12 h / 20 °C

3.1: NaH; imidazole / tetrahydrofuran / 7 h / 20 °C

3.2: 90 percent / tetrahydrofuran / 12 h / 20 °C

With 1H-imidazole; sodium hydride; di(n-butyl)tin oxide; In tetrahydrofuran; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4020(03)01103-7

Reference yield:

methyl α-D-galactopyranoside 3-benzyl ether (40010-11-5,61277-64-3,65942-01-0,81371-53-1,93714-01-3,108644-64-0,133268-63-0,133268-64-1,143005-10-1,143005-11-2,81371-52-0) → methyl 3-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,4-bis-O-(methylsulfanylthiocarbonyl)-α-D-galactopyranoside (614752-11-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 87 percent / imidazole / dimethylformamide / 12 h / 20 °C

2.1: NaH; imidazole / tetrahydrofuran / 7 h / 20 °C

2.2: 90 percent / tetrahydrofuran / 12 h / 20 °C

With 1H-imidazole; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(03)01103-7

upstream raw materials:

carbon disulfide

methyl-6-(tert-butyldimethylsilyloxy)-3-O-benzyl-α-D-galactopyranoside

methyl iodide

benzyl bromide

Downstream raw materials:

(2S,4S,6S)-4-(benzyloxy)-2-[(tert-butyldimethylsiloxy)methyl]-6-methoxytetrahydro-2H-pyran

[(2S,4S,6S)-4-(benzyloxy)-6-methoxytetrahydro-pyran-2-yl]-methanol

(2S,4S,6S)-4-Benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde

methyl 3-O-benzyl-2,4,6-trideoxy-α-D-threo-hept-6-ynopyranoside