Benzoic acid (2S,3R,4S,5R,6S)-2-((2R,3R,4S,5R,6S)-5-benzyloxy-2-benzyloxymethyl-4,6-dimethoxy-tetrahydro-pyran-3-yloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-4-methoxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2S,3R,4S,5R,6S)-2-((2R,3R,4S,5R,6S)-5-benzyloxy-2-benzyloxymethyl-4,6-dimethoxy-tetrahydro-pyran-3-yloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-4-methoxy-tetrahydro-pyran-3-yl ester
• CAS No.: 1053264-45-1
• Molecular Formula: C₄₂H₅₈O₁₂Si
• Molecular Weight: 783.001

Synonyms:Benzoic acid (2S,3R,4S,5R,6S)-2-((2R,3R,4S,5R,6S)-5-benzyloxy-2-benzyloxymethyl-4,6-dimethoxy-tetrahydro-pyran-3-yloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-4-methoxy-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2S,3R,4S,5R,6S)-2-((2R,3R,4S,5R,6S)-5-benzyloxy-2-benzyloxymethyl-4,6-dimethoxy-tetrahydro-pyran-3-yloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-4-methoxy-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of Benzoic acid (2S,3R,4S,5R,6S)-2-((2R,3R,4S,5R,6S)-5-benzyloxy-2-benzyloxymethyl-4,6-dimethoxy-tetrahydro-pyran-3-yloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-4-methoxy-tetrahydro-pyran-3-yl ester

There total 6 articles about Benzoic acid (2S,3R,4S,5R,6S)-2-((2R,3R,4S,5R,6S)-5-benzyloxy-2-benzyloxymethyl-4,6-dimethoxy-tetrahydro-pyran-3-yloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-4-methoxy-tetrahydro-pyran-3-yl ester 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 O-(benzyl 2-O-benzoyl-3-O-methyl-α-L-idopyranosyl)-(1->4)-2,6-di-O-benzyl-3-O-methyl-α-D-glucopyranoside (189390-20-3) → Benzoic acid (2S,3R,4S,5R,6S)-2-((2R,3R,4S,5R,6S)-5-benzyloxy-2-benzyloxymethyl-4,6-dimethoxy-tetrahydro-pyran-3-yloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-4-methoxy-tetrahydro-pyran-3-yl ester (1053264-45-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 50 ℃; for 4h;

DOI:10.1021/jm960726z

Reference yield:

methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (76375-66-1) → Benzoic acid (2S,3R,4S,5R,6S)-2-((2R,3R,4S,5R,6S)-5-benzyloxy-2-benzyloxymethyl-4,6-dimethoxy-tetrahydro-pyran-3-yloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-4-methoxy-tetrahydro-pyran-3-yl ester (1053264-45-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 79 percent / NaH / dimethylformamide / 1 h

2: 70 percent / HBF₄, NaBH₃CN / tetrahydrofuran; diethyl ether / 1.25 h

3: 89 percent / triflic acid, N-iodosuccinimide, 4A molecular sieves / toluene / 1 h

4: aq. CF₃CO₂H / CH₂Cl₂ / 0.67 h / Ambient temperature

5: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h / 50 °C

With dmap; N-iodo-succinimide; tetrafluoroboric acid; trifluorormethanesulfonic acid; 4 A molecular sieve; sodium hydride; sodium cyanoborohydride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm960726z

Reference yield:

ethyl 2-O-benzoyl-4,6-O-isopropylidene-3-O-methyl-1-thio-L-idopyranoside → Benzoic acid (2S,3R,4S,5R,6S)-2-((2R,3R,4S,5R,6S)-5-benzyloxy-2-benzyloxymethyl-4,6-dimethoxy-tetrahydro-pyran-3-yloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-4-methoxy-tetrahydro-pyran-3-yl ester (1053264-45-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / triflic acid, N-iodosuccinimide, 4A molecular sieves / toluene / 1 h

2: aq. CF₃CO₂H / CH₂Cl₂ / 0.67 h / Ambient temperature

3: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h / 50 °C

With dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; triethylamine; trifluoroacetic acid; In dichloromethane; toluene;

DOI:10.1021/jm960726z

upstream raw materials:

tert-butyldimethylsilyl chloride

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

methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

methyl 2-O-benzyl-4,6-O-benzylidene-3-O-methyl-α-D-glucopyranoside

Downstream raw materials:

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

methyl O-(benzyl 2-O-benzoyl-4-O-levulinyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,6-di-O-benzyl-3-O-methyl-α-D-glucopyranoside

methyl (2-O-benzoyl-4-O-levulinyl-3-O-methyl-α-L-idopyranosyluronic acid)-(1->4)-2,6-di-O-benzyl-3-O-methyl-α-D-glucopyranoside

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

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