Benzoic acid (2S,3S,4S,5S,6S)-4,5-bis-benzyloxy-6-[(R)-1-benzyloxy-2-(dimethyl-phenyl-silanyl)-ethyl]-2-[(2R,3R,4S,5S,6S)-3,5-bis-benzyloxy-2-((R)-1,2-bis-benzyloxy-ethyl)-6-methoxy-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2S,3S,4S,5S,6S)-4,5-bis-benzyloxy-6-[(R)-1-benzyloxy-2-(dimethyl-phenyl-silanyl)-ethyl]-2-[(2R,3R,4S,5S,6S)-3,5-bis-benzyloxy-2-((R)-1,2-bis-benzyloxy-ethyl)-6-methoxy-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester
• CAS No.: 195192-44-0
• Molecular Formula: C₇₉H₈₄O₁₃Si
• Molecular Weight: 1269.61

Synonyms:Benzoic acid (2S,3S,4S,5S,6S)-4,5-bis-benzyloxy-6-[(R)-1-benzyloxy-2-(dimethyl-phenyl-silanyl)-ethyl]-2-[(2R,3R,4S,5S,6S)-3,5-bis-benzyloxy-2-((R)-1,2-bis-benzyloxy-ethyl)-6-methoxy-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2S,3S,4S,5S,6S)-4,5-bis-benzyloxy-6-[(R)-1-benzyloxy-2-(dimethyl-phenyl-silanyl)-ethyl]-2-[(2R,3R,4S,5S,6S)-3,5-bis-benzyloxy-2-((R)-1,2-bis-benzyloxy-ethyl)-6-methoxy-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

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Technology Process of Benzoic acid (2S,3S,4S,5S,6S)-4,5-bis-benzyloxy-6-[(R)-1-benzyloxy-2-(dimethyl-phenyl-silanyl)-ethyl]-2-[(2R,3R,4S,5S,6S)-3,5-bis-benzyloxy-2-((R)-1,2-bis-benzyloxy-ethyl)-6-methoxy-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester

There total 13 articles about Benzoic acid (2S,3S,4S,5S,6S)-4,5-bis-benzyloxy-6-[(R)-1-benzyloxy-2-(dimethyl-phenyl-silanyl)-ethyl]-2-[(2R,3R,4S,5S,6S)-3,5-bis-benzyloxy-2-((R)-1,2-bis-benzyloxy-ethyl)-6-methoxy-tetrahydro-pyran-4-yloxy]-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: 76.0%

(2R,3S,4S,5S,6S)-3,5-Bis-benzyloxy-2-((R)-1,2-bis-benzyloxy-ethyl)-6-methoxy-tetrahydro-pyran-4-ol + Benzoic acid (2R,3S,4S,5S,6S)-4,5-bis-benzyloxy-6-[(R)-1-benzyloxy-2-(dimethyl-phenyl-silanyl)-ethyl]-2-ethylsulfanyl-tetrahydro-pyran-3-yl ester (195192-42-8) → Benzoic acid (2S,3S,4S,5S,6S)-4,5-bis-benzyloxy-6-[(R)-1-benzyloxy-2-(dimethyl-phenyl-silanyl)-ethyl]-2-[(2R,3R,4S,5S,6S)-3,5-bis-benzyloxy-2-((R)-1,2-bis-benzyloxy-ethyl)-6-methoxy-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester (195192-44-0)

Guidance literature:

With N-iodo-succinimide; molecular sieve; trifluorormethanesulfonic acid; In tetrahydrofuran; 1,2-dichloro-ethane; at 0 ℃; for 0.25h;

Reference yield:

ethyl 1-thio-α-D-mannopyranoside (7473-36-1,13533-58-9,36400-88-1,56245-60-4,73494-52-7,73804-33-8,128946-17-8,686299-00-3) → Benzoic acid (2S,3S,4S,5S,6S)-4,5-bis-benzyloxy-6-[(R)-1-benzyloxy-2-(dimethyl-phenyl-silanyl)-ethyl]-2-[(2R,3R,4S,5S,6S)-3,5-bis-benzyloxy-2-((R)-1,2-bis-benzyloxy-ethyl)-6-methoxy-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester (195192-44-0)

Guidance literature:

Multi-step reaction with 11 steps

1: pyridine / 5 h

2: 70 percent / CSA / acetone / 16 h

3: 76 percent / NaH, TBAI / dimethylformamide / 5 h

4: 78 percent / pyrrole, TFA / CH₂Cl₂ / 0.17 h / 0 °C

5: 1.) (COCl)2, DMSO, 2.) DIPEA / 1.) CH₂Cl₂, -60 deg C, 30 min, 2.) -60 deg C -> room temperature

6: 1.) Mg, 1,2-dibromoethane / 1.) Et₂O, reflux, 2.) Et₂O, 0 deg C, 1 h

7: 82 percent / NaH, TBAI / dimethylformamide / 5 h

8: AcOH, H₂O / 16 h / 50 °C

9: 1.) Bu₂SnO, 2.) CsF, NaI / 11.) MeOH, reflux, 2.) DMF, 16 h

10: 89 percent / pyridine / 1 h

11: 76 percent / NIS, TfOH, molecular sieves / tetrahydrofuran; 1,2-dichloro-ethane / 0.25 h / 0 °C

With N-iodo-succinimide; pyrrole; molecular sieve; oxalyl dichloride; trifluorormethanesulfonic acid; camphor-10-sulfonic acid; water; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; magnesium; acetic acid; dimethyl sulfoxide; ethylene dibromide; N-ethyl-N,N-diisopropylamine; cesium fluoride; trifluoroacetic acid; sodium iodide; In tetrahydrofuran; pyridine; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone;

Reference yield:

ethyl 1-thio-6-O-triphenylmethyl-α-D-mannopyranoside (128850-48-6) → Benzoic acid (2S,3S,4S,5S,6S)-4,5-bis-benzyloxy-6-[(R)-1-benzyloxy-2-(dimethyl-phenyl-silanyl)-ethyl]-2-[(2R,3R,4S,5S,6S)-3,5-bis-benzyloxy-2-((R)-1,2-bis-benzyloxy-ethyl)-6-methoxy-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester (195192-44-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 70 percent / CSA / acetone / 16 h

2: 76 percent / NaH, TBAI / dimethylformamide / 5 h

3: 78 percent / pyrrole, TFA / CH₂Cl₂ / 0.17 h / 0 °C

4: 1.) (COCl)2, DMSO, 2.) DIPEA / 1.) CH₂Cl₂, -60 deg C, 30 min, 2.) -60 deg C -> room temperature

5: 1.) Mg, 1,2-dibromoethane / 1.) Et₂O, reflux, 2.) Et₂O, 0 deg C, 1 h

6: 82 percent / NaH, TBAI / dimethylformamide / 5 h

7: AcOH, H₂O / 16 h / 50 °C

8: 1.) Bu₂SnO, 2.) CsF, NaI / 11.) MeOH, reflux, 2.) DMF, 16 h

9: 89 percent / pyridine / 1 h

10: 76 percent / NIS, TfOH, molecular sieves / tetrahydrofuran; 1,2-dichloro-ethane / 0.25 h / 0 °C

With N-iodo-succinimide; pyrrole; molecular sieve; oxalyl dichloride; trifluorormethanesulfonic acid; camphor-10-sulfonic acid; water; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; magnesium; acetic acid; dimethyl sulfoxide; ethylene dibromide; N-ethyl-N,N-diisopropylamine; cesium fluoride; trifluoroacetic acid; sodium iodide; In tetrahydrofuran; pyridine; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone;

upstream raw materials:

Benzoic acid (2R,3S,4S,5S,6S)-4,5-bis-benzyloxy-6-[(R)-1-benzyloxy-2-(dimethyl-phenyl-silanyl)-ethyl]-2-ethylsulfanyl-tetrahydro-pyran-3-yl ester

ethyl 1-thio-α-D-mannopyranoside

ethyl 1-thio-6-O-triphenylmethyl-α-D-mannopyranoside

ethyl 4-O-benzyl-2,3-O-isoproylidene-1-thio-α-D-mannopyranoside

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