tert-Butyl-[(2S,3R,4S,5S,6R)-5-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-dimethyl-silane

Base Information

• Chemical Name: tert-Butyl-[(2S,3R,4S,5S,6R)-5-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-dimethyl-silane
• CAS No.: 256413-34-0
• Molecular Formula: C₂₇H₄₀O₅SSi
• Molecular Weight: 504.763

Synonyms:tert-Butyl-[(2S,3R,4S,5S,6R)-5-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-dimethyl-silane

Chemical Property of tert-Butyl-[(2S,3R,4S,5S,6R)-5-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-dimethyl-silane

Chemical Property:

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Technology Process of tert-Butyl-[(2S,3R,4S,5S,6R)-5-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-dimethyl-silane

There total 10 articles about tert-Butyl-[(2S,3R,4S,5S,6R)-5-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-dimethyl-silane 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: 94.0%

(2R,3S,4S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol (256413-33-9) + methyl iodide (74-88-4) → tert-Butyl-[(2S,3R,4S,5S,6R)-5-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-dimethyl-silane (256413-34-0)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 - 25 ℃; for 1h;

DOI:10.1002/(SICI)1521-3773(19991115)38:22<3345::AID-ANIE3345>3.0.CO;2-9

Reference yield:

phenyl 4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside (71676-30-7,87508-17-6,138922-03-9,87508-18-7) → tert-Butyl-[(2S,3R,4S,5S,6R)-5-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-dimethyl-silane (256413-34-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: nBu₂SnO / toluene / 3 h / Heating

1.2: 87 percent / nBu₄NI / 2 h / 25 - 110 °C

2.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 - 25 °C

3.1: 77 percent / EtSH; Zn(OTf)2 / CH₂Cl₂ / 2 h / 0 °C

4.1: 97 percent / pyridine / 12 h / 0 - 25 °C

5.1: 90 percent / LAH / tetrahydrofuran / 3 h / 0 - 45 °C

6.1: NaH / dimethylformamide / 0.08 h / 0 °C

6.2: 94 percent / dimethylformamide / 1 h / 0 - 25 °C

With pyridine; 2,6-dimethylpyridine; lithium aluminium tetrahydride; zinc trifluoromethanesulfonate; sodium hydride; di(n-butyl)tin oxide; ethanethiol; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Cyclization / 1.2: Ring cleavage / 2.1: Etherification / 3.1: Ring cleavage / 4.1: Tosylation / 5.1: Reduction / 6.1: Metallation / 6.2: Methylation;

DOI:10.1002/1521-3765(20000901)6:17<3149::AID-CHEM3149>3.0.CO;2-L

Reference yield:

phenyl 4,6-O-benzylidene-3-O-(p-methoxybenzyl)-1-thio-β-D-galactopyranoside (179072-68-5) → tert-Butyl-[(2S,3R,4S,5S,6R)-5-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-dimethyl-silane (256413-34-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 - 25 °C

2.1: 77 percent / EtSH; Zn(OTf)2 / CH₂Cl₂ / 2 h / 0 °C

3.1: 97 percent / pyridine / 12 h / 0 - 25 °C

4.1: 90 percent / LAH / tetrahydrofuran / 3 h / 0 - 45 °C

5.1: NaH / dimethylformamide / 0.08 h / 0 °C

5.2: 94 percent / dimethylformamide / 1 h / 0 - 25 °C

With pyridine; 2,6-dimethylpyridine; lithium aluminium tetrahydride; zinc trifluoromethanesulfonate; sodium hydride; ethanethiol; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: Etherification / 2.1: Ring cleavage / 3.1: Tosylation / 4.1: Reduction / 5.1: Metallation / 5.2: Methylation;

DOI:10.1002/1521-3765(20000901)6:17<3149::AID-CHEM3149>3.0.CO;2-L

upstream raw materials:

(2R,3S,4S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol

methyl iodide

t-butyldimethylsiyl triflate

phenyl 4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside

Downstream raw materials:

(2S,3R,4S,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran

Acetic acid (2S,3S,4S,5R,6R)-2-((3R,4S,5S,6R)-2,3-diacetoxy-5-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-4-hydroxy-5-(4-methoxy-benzyloxy)-4,6-dimethyl-tetrahydro-pyran-3-yl ester

(2R,4aR,6S,7R,8aR)-7-(tert-Butyl-dimethyl-silanyloxy)-6-[(2S,3R,4S,5S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-4-yloxy]-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one

(2R,4aR,6S,7S,8S,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-[(2S,3R,4S,5S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

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