(2R,3S,4R,5R,6R)-4-Benzyloxy-5-(4-methoxy-benzyloxy)-6-methoxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: (2R,3S,4R,5R,6R)-4-Benzyloxy-5-(4-methoxy-benzyloxy)-6-methoxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol
• CAS No.: 256341-92-1
• Molecular Formula: C₂₈H₃₂O₆S
• Molecular Weight: 496.624

Synonyms:(2R,3S,4R,5R,6R)-4-Benzyloxy-5-(4-methoxy-benzyloxy)-6-methoxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol

Chemical Property of (2R,3S,4R,5R,6R)-4-Benzyloxy-5-(4-methoxy-benzyloxy)-6-methoxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol

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Technology Process of (2R,3S,4R,5R,6R)-4-Benzyloxy-5-(4-methoxy-benzyloxy)-6-methoxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol

There total 6 articles about (2R,3S,4R,5R,6R)-4-Benzyloxy-5-(4-methoxy-benzyloxy)-6-methoxymethyl-2-phenylsulfanyl-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: 89.0%

benzyl bromide (100-39-0) + (2R,3S,4R,5S,6R)-5-(4-Methoxy-benzyloxy)-6-methoxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3,4-diol (256341-91-0) → (2R,3S,4R,5R,6R)-4-Benzyloxy-5-(4-methoxy-benzyloxy)-6-methoxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol (256341-92-1)

Guidance literature:

(2R,3S,4R,5S,6R)-5-(4-Methoxy-benzyloxy)-6-methoxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3,4-diol; With di(n-butyl)tin oxide; In toluene; at 110 ℃; for 3h;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In toluene; at 25 - 110 ℃; for 5h;

DOI:10.1002/(SICI)1521-3773(19991115)38:22<3340::AID-ANIE3340>3.0.CO;2-2

Reference yield:

phenyl 2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside (126092-08-8) → (2R,3S,4R,5R,6R)-4-Benzyloxy-5-(4-methoxy-benzyloxy)-6-methoxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol (256341-92-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

2.1: NaH / dimethylformamide; tetrahydrofuran / 0.25 h / 0 °C

2.2: 95 percent / nBu₄NI / dimethylformamide; tetrahydrofuran / 4 h / 0 - 25 °C

3.1: 95 percent / TBAF / tetrahydrofuran / 1 h / 25 °C

4.1: NaH / dimethylformamide / 0.25 h / 0 °C

4.2: 95 percent / dimethylformamide / 1 h / 0 - 25 °C

5.1: 85 percent / TsOH; (CH₂OH)2 / methanol / 5 h / 25 °C

6.1: nBu₂SnO / toluene / 3 h / Heating

6.2: 89 percent / nBu₄NI / toluene / 5 h / 25 - 110 °C

With 2,6-dimethylpyridine; tetrabutyl ammonium fluoride; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; ethylene glycol; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Etherification / 2.1: Metallation / 2.2: Etherification / 3.1: Silyl ether cleavage / 4.1: Metallation / 4.2: Methylation / 5.1: Ring cleavage / 6.1: Cyclization / 6.2: Ring cleavage;

DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8

Reference yield:

(3aS,4R,6R,7R,7aS)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-4-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol (256341-88-5) → (2R,3S,4R,5R,6R)-4-Benzyloxy-5-(4-methoxy-benzyloxy)-6-methoxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol (256341-92-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaH / dimethylformamide; tetrahydrofuran / 0.25 h / 0 °C

1.2: 95 percent / nBu₄NI / dimethylformamide; tetrahydrofuran / 4 h / 0 - 25 °C

2.1: 95 percent / TBAF / tetrahydrofuran / 1 h / 25 °C

3.1: NaH / dimethylformamide / 0.25 h / 0 °C

3.2: 95 percent / dimethylformamide / 1 h / 0 - 25 °C

4.1: 85 percent / TsOH; (CH₂OH)2 / methanol / 5 h / 25 °C

5.1: nBu₂SnO / toluene / 3 h / Heating

5.2: 89 percent / nBu₄NI / toluene / 5 h / 25 - 110 °C

With tetrabutyl ammonium fluoride; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; ethylene glycol; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene; 1.1: Metallation / 1.2: Etherification / 2.1: Silyl ether cleavage / 3.1: Metallation / 3.2: Methylation / 4.1: Ring cleavage / 5.1: Cyclization / 5.2: Ring cleavage;

DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8

upstream raw materials:

benzyl bromide

(2R,3S,4R,5S,6R)-5-(4-Methoxy-benzyloxy)-6-methoxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3,4-diol

phenyl 2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside

(3aS,4R,6R,7R,7aS)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-4-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol

Downstream raw materials:

(2R,3S,4R,5R,6R)-4-Benzyloxy-5-(4-methoxy-benzyloxy)-6-methoxymethyl-tetrahydro-pyran-2,3-diol

(2R,3R,4S,5S,6S)-4-Benzyloxy-6-((2S,3R,4R,5S)-4,5-bis-allyloxy-3-benzyloxy-tetrahydro-pyran-2-yloxy)-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-ol

(2S,3R,4S,5S)-4,5-Bis-allyloxy-2-[(2S,3S,4S,5R,6R)-4-benzyloxy-3-methoxy-5-(4-methoxy-benzyloxy)-6-methoxymethyl-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-3-ol

(3S,4R,5R,6S)-5-Benzyloxy-6-((2S,3S,4R,5R,6R)-4-benzyloxy-3-methoxy-6-methoxymethyl-5-triisopropylsilanyloxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3,4-diol

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