(2S,3R,4S,5R,6S)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dimethoxy-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: (2S,3R,4S,5R,6S)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dimethoxy-tetrahydro-pyran-3-ol
• CAS No.: 200712-60-3
• Molecular Formula: C₄₂H₆₀O₁₁Si
• Molecular Weight: 769.017

Synonyms:

Chemical Property of (2S,3R,4S,5R,6S)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dimethoxy-tetrahydro-pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5R,6S)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dimethoxy-tetrahydro-pyran-3-ol

There total 6 articles about (2S,3R,4S,5R,6S)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dimethoxy-tetrahydro-pyran-3-ol 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:

tert-butyldimethylsilyl chloride (18162-48-6) + methyl(2,3-di-O-methyl-α-L-idopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside (200712-58-9) → (2S,3R,4S,5R,6S)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dimethoxy-tetrahydro-pyran-3-ol (200712-60-3)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 50 ℃; for 3h;

DOI:10.1016/S0008-6215(99)00067-1

Reference yield:

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) → (2S,3R,4S,5R,6S)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dimethoxy-tetrahydro-pyran-3-ol (200712-60-3)

Guidance literature:

Multi-step reaction with 5 steps

1: triflic acid; NIS; 4A molecular sieves / toluene / 2 h / -20 °C

2: 86 percent / NaOMe / methanol; CH₂Cl₂ / 1 h

3: 32.1 g / NaH / dimethylformamide / 20 °C

4: 27.5 g / CF₃COOH; water / CH₂Cl₂ / 0.42 h / 20 °C

5: triethylamine; DMAP / CH₂Cl₂ / 3 h / 50 °C

With dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; water; sodium methylate; sodium hydride; triethylamine; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Etherification / 2: debenzoylation / 3: Methylation / 4: Hydrolysis / 5: Etherification;

DOI:10.1016/S0008-6215(99)00067-1

Reference yield:

ethyl 2-O-benzoyl-4,6-O-isopropylidene-3-O-methyl-1-thio-L-idopyranoside → (2S,3R,4S,5R,6S)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dimethoxy-tetrahydro-pyran-3-ol (200712-60-3)

Guidance literature:

Multi-step reaction with 5 steps

1: triflic acid; NIS; 4A molecular sieves / toluene / 2 h / -20 °C

2: 86 percent / NaOMe / methanol; CH₂Cl₂ / 1 h

3: 32.1 g / NaH / dimethylformamide / 20 °C

4: 27.5 g / CF₃COOH; water / CH₂Cl₂ / 0.42 h / 20 °C

5: triethylamine; DMAP / CH₂Cl₂ / 3 h / 50 °C

With dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; water; sodium methylate; sodium hydride; triethylamine; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Etherification / 2: debenzoylation / 3: Methylation / 4: Hydrolysis / 5: Etherification;

DOI:10.1016/S0008-6215(99)00067-1

upstream raw materials:

tert-butyldimethylsilyl chloride

methyl(2,3-di-O-methyl-α-L-idopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

methyl(4,6-O-isopropylidene-2,3-di-O-methyl-α-L-idopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

Downstream raw materials:

methyl (6-O-tert-butyldimethylsilyl-4-O-levulinyl-2,3-di-O-methyl-α-L-idopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

(benzyl 4-O-levulinyl-2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-1,3,6-tri-O-acetyl-2-O-benzyl-D-glucopyranose

(2R,3S,4S,5R,6R)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-4,5-dimethoxy-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid

(benzyl 4-O-levulinyl-2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-3,6-di-O-acetyl-2-O-benzyl-1-O-trichloroacetimidoyl-D-glucopyranose

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