(2S,3R,4R,5R)-2-Ethylsulfanyl-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: (2S,3R,4R,5R)-2-Ethylsulfanyl-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol
• CAS No.: 335197-25-6
• Molecular Formula: C₂₃H₃₀O₆S
• Molecular Weight: 434.554

Synonyms:(2S,3R,4R,5R)-2-Ethylsulfanyl-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol

Chemical Property of (2S,3R,4R,5R)-2-Ethylsulfanyl-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol

Chemical Property:

Purity/Quality:

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Technology Process of (2S,3R,4R,5R)-2-Ethylsulfanyl-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol

There total 8 articles about (2S,3R,4R,5R)-2-Ethylsulfanyl-4,5-bis-(4-methoxy-benzyloxy)-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: 93.0%

Acetic acid (2S,3R,4S,5R)-2-ethylsulfanyl-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester (335197-24-5) → (2S,3R,4R,5R)-2-Ethylsulfanyl-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol (335197-25-6)

Guidance literature:

With sodium methylate; In methanol; at 25 ℃; for 4h;

DOI:10.1016/j.tet.2016.05.049

Reference yield:

1,2,3,4-tetra-O-acetyl-D-xylopyranose (62446-93-9) → (2S,3R,4R,5R)-2-Ethylsulfanyl-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol (335197-25-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 93 percent / HBr; AcOH / CH₂Cl₂ / 4 h / 0 - 25 °C

2.1: 82 percent / 2,6-lutidine / nitromethane / 12 h / 25 °C

3.1: NaOMe / methanol / 3 h / 25 °C

4.1: NaH / tetrahydrofuran / 0 °C

4.2: 5.14 g / tetrabutylammonium chloride / tetrahydrofuran / 4 h / Heating

5.1: ZnCl₂ / CH₂Cl₂ / -60 - 0 °C

6.1: 3.4 g / NaOMe / methanol / 4 h / 25 °C

With 2,6-dimethylpyridine; hydrogen bromide; sodium methylate; sodium hydride; acetic acid; zinc(II) chloride; In tetrahydrofuran; methanol; nitromethane; dichloromethane;

DOI:10.1021/ja012119t

Reference yield:

(S)-1,2-O-(1-ethylthioethylidene)-α-D-xylopyranose (335197-22-3) → (2S,3R,4R,5R)-2-Ethylsulfanyl-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol (335197-25-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 0 °C

1.2: 5.14 g / tetrabutylammonium chloride / tetrahydrofuran / 4 h / Heating

2.1: ZnCl₂ / CH₂Cl₂ / -60 - 0 °C

3.1: 3.4 g / NaOMe / methanol / 4 h / 25 °C

With sodium methylate; sodium hydride; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ja012119t

upstream raw materials:

Acetic acid (2S,3R,4S,5R)-2-ethylsulfanyl-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester

2,3,4-tri-O-acetyl-α-D-xylopyranosyl bromide

1,2,3,4-tetra-O-acetyl-D-xylopyranose

p-methoxybenzyl chloride

Downstream raw materials:

4-Methoxy-benzoic acid (2S,3R,4S,5R)-2-ethylsulfanyl-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester

3β,16β,17α-trihydroxycholest-5-en-22-one 16-O-{O-[2-O-(4-methoxybenzoyl)-β-D-xylopyranosyl]-(1->3)-2-O-acetyl-β-L-arabinopyranoside}

4-Methoxy-benzoic acid (3R,4S,5R)-4,5-bis-(4-methoxy-benzyloxy)-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

4-Methoxy-benzoic acid (2S,3R,4S,5R)-2-((2S,3R,4R,5S)-3-acetoxy-2-phenylsulfanyl-5-triethylsilanyloxy-tetrahydro-pyran-4-yloxy)-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester

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