(2R,3S,4S,5R,6S)-3-Benzyloxy-2-hydroxymethyl-5-isopropoxy-6-p-tolylsulfanyl-tetrahydro-pyran-4-ol

Base Information

• Chemical Name: (2R,3S,4S,5R,6S)-3-Benzyloxy-2-hydroxymethyl-5-isopropoxy-6-p-tolylsulfanyl-tetrahydro-pyran-4-ol
• CAS No.: 862851-27-2
• Molecular Formula: C₂₃H₃₀O₅S
• Molecular Weight: 418.554

Synonyms:(2R,3S,4S,5R,6S)-3-Benzyloxy-2-hydroxymethyl-5-isopropoxy-6-p-tolylsulfanyl-tetrahydro-pyran-4-ol

Chemical Property of (2R,3S,4S,5R,6S)-3-Benzyloxy-2-hydroxymethyl-5-isopropoxy-6-p-tolylsulfanyl-tetrahydro-pyran-4-ol

Chemical Property:

Purity/Quality:

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MSDS Files:

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Technology Process of (2R,3S,4S,5R,6S)-3-Benzyloxy-2-hydroxymethyl-5-isopropoxy-6-p-tolylsulfanyl-tetrahydro-pyran-4-ol

There total 4 articles about (2R,3S,4S,5R,6S)-3-Benzyloxy-2-hydroxymethyl-5-isopropoxy-6-p-tolylsulfanyl-tetrahydro-pyran-4-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: 72.0%

4-methylphenyl 2,3-di-O-isoporpylidene-4,6-O-benzylidene-1-thio-β-D-glucopyranoside (862851-26-1) → (2R,3S,4S,5R,6S)-3-Benzyloxy-2-hydroxymethyl-5-isopropoxy-6-p-tolylsulfanyl-tetrahydro-pyran-4-ol (862851-27-2) + 4-methylphenyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside (219518-19-1)

Guidance literature:

With borane-THF; vanadyl triflate; In tetrahydrofuran; dichloromethane; at 0 - 20 ℃;

DOI:10.1021/ol051178z

Reference yield:

p-methylphenyl 1-thio-β-D-glucopyranoside (1152-39-2) → (2R,3S,4S,5R,6S)-3-Benzyloxy-2-hydroxymethyl-5-isopropoxy-6-p-tolylsulfanyl-tetrahydro-pyran-4-ol (862851-27-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / VO(OTf)2*xH₂O / acetonitrile / 8 h / 20 °C

2: 94 percent / D-camphorsulfonic acid / tetrahydrofuran / 1.5 h / 20 °C

3: 72 percent / VO(OTf)2; BH₃*THF / CH₂Cl₂; tetrahydrofuran / 0 - 20 °C

With borane-THF; vanadyl triflate; (1S)-10-camphorsulfonic acid; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/ol051178z

Reference yield:

benzaldehyde (100-52-7) → (2R,3S,4S,5R,6S)-3-Benzyloxy-2-hydroxymethyl-5-isopropoxy-6-p-tolylsulfanyl-tetrahydro-pyran-4-ol (862851-27-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / VO(OTf)2*xH₂O / acetonitrile / 8 h / 20 °C

2: 94 percent / D-camphorsulfonic acid / tetrahydrofuran / 1.5 h / 20 °C

3: 72 percent / VO(OTf)2; BH₃*THF / CH₂Cl₂; tetrahydrofuran / 0 - 20 °C

With borane-THF; vanadyl triflate; (1S)-10-camphorsulfonic acid; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/ol051178z

upstream raw materials:

4-methylphenyl 2,3-di-O-isoporpylidene-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

p-methylphenyl 1-thio-β-D-glucopyranoside

benzaldehyde

4-methylphenyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside

Downstream raw materials:

4-methylphenyl (6-O-acetyl-4-O-benzyl-2-O-isopropyl)-1-thio-β-D-glucopyranoside

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