[(Z)-1-Benzenesulfonyl-2-((2S,4R,5S,6S)-4-benzyloxy-5,6-dimethoxy-tetrahydro-pyran-2-yl)-vinyl]-trimethyl-silane

Base Information

• Chemical Name: [(Z)-1-Benzenesulfonyl-2-((2S,4R,5S,6S)-4-benzyloxy-5,6-dimethoxy-tetrahydro-pyran-2-yl)-vinyl]-trimethyl-silane
• CAS No.: 78462-71-2
• Molecular Formula: C₂₅H₃₄O₆SSi
• Molecular Weight: 490.693

Synonyms:[(Z)-1-Benzenesulfonyl-2-((2S,4R,5S,6S)-4-benzyloxy-5,6-dimethoxy-tetrahydro-pyran-2-yl)-vinyl]-trimethyl-silane

Chemical Property of [(Z)-1-Benzenesulfonyl-2-((2S,4R,5S,6S)-4-benzyloxy-5,6-dimethoxy-tetrahydro-pyran-2-yl)-vinyl]-trimethyl-silane

Chemical Property:

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Technology Process of [(Z)-1-Benzenesulfonyl-2-((2S,4R,5S,6S)-4-benzyloxy-5,6-dimethoxy-tetrahydro-pyran-2-yl)-vinyl]-trimethyl-silane

There total 16 articles about [(Z)-1-Benzenesulfonyl-2-((2S,4R,5S,6S)-4-benzyloxy-5,6-dimethoxy-tetrahydro-pyran-2-yl)-vinyl]-trimethyl-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:

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol (617-04-9) → [(Z)-1-Benzenesulfonyl-2-((2S,4R,5S,6S)-4-benzyloxy-5,6-dimethoxy-tetrahydro-pyran-2-yl)-vinyl]-trimethyl-silane (78462-71-2)

Guidance literature:

Multi-step reaction with 12 steps

1: 47.1 percent / pyridinium p-toluenesulfonate / acetone; dimethylformamide / 36 h / 5 °C

2: 53.2 g / CH₂Cl₂; pyridine / 60 h

3: 60 percent / NaH / tetrahydrofuran / 1.5 h / Ambient temperature

4: 100 percent / Dowex 50W (H+) / methanol / 3.5 h / Ambient temperature

5: 86 percent / pyridine / 1.5 h / 70 °C

6: 86 percent / t-BuOK / tetrahydrofuran / 0.5 h / 0 °C

7: LiBEt₃H / tetrahydrofuran / 120 h / -20 °C

8: 15.4 g / NaH / dimethylsulfoxide; tetrahydrofuran / 24 h / Ambient temperature

9: HCl / CHCl₃ / Ambient temperature

10: oxalyl chloride / CH₂Cl₂; dimethylsulfoxide / 0.25 h / -70 °C

11: 72 percent / n-BuLi / hexane; tetrahydrofuran / -45 deg C, 5 min; RT, 30 min

12: MCPBA / CH₂Cl₂ / 0.5 h / 0 °C

With hydrogenchloride; n-butyllithium; oxalyl dichloride; Dowex 50W (H+); potassium tert-butylate; sodium hydride; lithium triethylborohydride; 3-chloro-benzenecarboperoxoic acid; pyridinium p-toluenesulfonate; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; chloroform; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ja00323a032

Reference yield:

[(E)-2-((2S,4R,5S,6S)-4-Benzyloxy-5,6-dimethoxy-tetrahydro-pyran-2-yl)-1-phenylsulfanyl-vinyl]-trimethyl-silane → [(Z)-1-Benzenesulfonyl-2-((2S,4R,5S,6S)-4-benzyloxy-5,6-dimethoxy-tetrahydro-pyran-2-yl)-vinyl]-trimethyl-silane (78462-71-2) + [(E)-1-Benzenesulfonyl-2-((2S,4R,5S,6S)-4-benzyloxy-5,6-dimethoxy-tetrahydro-pyran-2-yl)-vinyl]-trimethyl-silane (78462-72-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 0.5h; Yield given;

DOI:10.1021/ja00323a032

Reference yield:

methyl 4,6-O-isopropylidene-α-D-mannopyranoside (63167-67-9) → [(Z)-1-Benzenesulfonyl-2-((2S,4R,5S,6S)-4-benzyloxy-5,6-dimethoxy-tetrahydro-pyran-2-yl)-vinyl]-trimethyl-silane (78462-71-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 53.2 g / CH₂Cl₂; pyridine / 60 h

2: 60 percent / NaH / tetrahydrofuran / 1.5 h / Ambient temperature

3: 100 percent / Dowex 50W (H+) / methanol / 3.5 h / Ambient temperature

4: 86 percent / pyridine / 1.5 h / 70 °C

5: 86 percent / t-BuOK / tetrahydrofuran / 0.5 h / 0 °C

6: LiBEt₃H / tetrahydrofuran / 120 h / -20 °C

7: 15.4 g / NaH / dimethylsulfoxide; tetrahydrofuran / 24 h / Ambient temperature

8: HCl / CHCl₃ / Ambient temperature

9: oxalyl chloride / CH₂Cl₂; dimethylsulfoxide / 0.25 h / -70 °C

10: 72 percent / n-BuLi / hexane; tetrahydrofuran / -45 deg C, 5 min; RT, 30 min

11: MCPBA / CH₂Cl₂ / 0.5 h / 0 °C

With hydrogenchloride; n-butyllithium; oxalyl dichloride; Dowex 50W (H+); potassium tert-butylate; sodium hydride; lithium triethylborohydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; chloroform; dimethyl sulfoxide;

DOI:10.1021/ja00323a032

upstream raw materials:

lithium bis(trimethylsilyl)(phenylthio)methylide

(2S,4R,5S,6S)-4-Benzyloxy-5,6-dimethoxy-tetrahydro-pyran-2-carbaldehyde

methyl 4,6-O-isopropylidene-α-D-mannopyranoside

α,α-bis(trimethylsilyl)methylphenyl sulfide

Downstream raw materials:

(2S,3S,4R,6S)-6-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-4-benzyloxy-2,3-dimethoxy-tetrahydro-pyran

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