Methanesulfonic acid (2S,3S)-3-benzyloxy-2-[(R)-1-((R)-1-benzyloxy-2-methanesulfonyloxy-ethyl)-but-3-enyloxy]-hex-5-enyl ester

Base Information

• Chemical Name: Methanesulfonic acid (2S,3S)-3-benzyloxy-2-[(R)-1-((R)-1-benzyloxy-2-methanesulfonyloxy-ethyl)-but-3-enyloxy]-hex-5-enyl ester
• CAS No.: 475276-07-4
• Molecular Formula: C₂₈H₃₈O₉S₂
• Molecular Weight: 582.736

Synonyms:Methanesulfonic acid (2S,3S)-3-benzyloxy-2-[(R)-1-((R)-1-benzyloxy-2-methanesulfonyloxy-ethyl)-but-3-enyloxy]-hex-5-enyl ester

Chemical Property of Methanesulfonic acid (2S,3S)-3-benzyloxy-2-[(R)-1-((R)-1-benzyloxy-2-methanesulfonyloxy-ethyl)-but-3-enyloxy]-hex-5-enyl ester

Chemical Property:

Purity/Quality:

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Technology Process of Methanesulfonic acid (2S,3S)-3-benzyloxy-2-[(R)-1-((R)-1-benzyloxy-2-methanesulfonyloxy-ethyl)-but-3-enyloxy]-hex-5-enyl ester

There total 13 articles about Methanesulfonic acid (2S,3S)-3-benzyloxy-2-[(R)-1-((R)-1-benzyloxy-2-methanesulfonyloxy-ethyl)-but-3-enyloxy]-hex-5-enyl ester 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: 100.0%

methanesulfonyl chloride (124-63-0) + (2R,3R)-2-Benzyloxy-3-((1S,2S)-2-benzyloxy-1-hydroxymethyl-pent-4-enyloxy)-hex-5-en-1-ol (475275-99-1) → Methanesulfonic acid (2S,3S)-3-benzyloxy-2-[(R)-1-((R)-1-benzyloxy-2-methanesulfonyloxy-ethyl)-but-3-enyloxy]-hex-5-enyl ester (475276-07-4)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 25 ℃; for 3.5h;

DOI:10.1055/s-2002-33511

Reference yield:

allyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside (53263-18-6,82659-53-8,98920-46-8,98920-48-0,98920-49-1,103773-87-1,98920-44-6) → Methanesulfonic acid (2S,3S)-3-benzyloxy-2-[(R)-1-((R)-1-benzyloxy-2-methanesulfonyloxy-ethyl)-but-3-enyloxy]-hex-5-enyl ester (475276-07-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 89 percent / MeONa / methanol / 48 h / 0 °C

2: imidazole / dimethylformamide / 0.5 h / 24 °C

3: CSA / 1.5 h / 24 °C

4: 99 percent / NaI; Bu₄NI / tetrahydrofuran / 30 h / 24 °C

5: 100 percent / TBAF / tetrahydrofuran / 2 h / 23 °C

6: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.42 h / -78 - 0 °C

7: LiClO₄ / diethyl ether / 23 h / 23 °C

8: 100 percent / NaH; Bu₄NI / tetrahydrofuran / 22 h / 25 °C

9: 94 percent / aq. HCl / tetrahydrofuran / 3.5 h / 23 °C

10: aq. NaIO₄ / methanol / 1.3 h / 23 °C / pH 7

11: NaBH₄ / methanol / 2 h / 0 - 23 °C

12: 100 percent / Et₃N / CH₂Cl₂ / 3.5 h / 0 - 25 °C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; sodium periodate; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium methylate; lithium perchlorate; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 6: Swern oxidation;

DOI:10.1055/s-2002-33511

Reference yield:

2,6-anhydro-7,8,9-trideoxy-D-glycero-L-galacto-non-8-enitol (133697-14-0) → Methanesulfonic acid (2S,3S)-3-benzyloxy-2-[(R)-1-((R)-1-benzyloxy-2-methanesulfonyloxy-ethyl)-but-3-enyloxy]-hex-5-enyl ester (475276-07-4)

Guidance literature:

Multi-step reaction with 11 steps

1: imidazole / dimethylformamide / 0.5 h / 24 °C

2: CSA / 1.5 h / 24 °C

3: 99 percent / NaI; Bu₄NI / tetrahydrofuran / 30 h / 24 °C

4: 100 percent / TBAF / tetrahydrofuran / 2 h / 23 °C

5: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.42 h / -78 - 0 °C

6: LiClO₄ / diethyl ether / 23 h / 23 °C

7: 100 percent / NaH; Bu₄NI / tetrahydrofuran / 22 h / 25 °C

8: 94 percent / aq. HCl / tetrahydrofuran / 3.5 h / 23 °C

9: aq. NaIO₄ / methanol / 1.3 h / 23 °C / pH 7

10: NaBH₄ / methanol / 2 h / 0 - 23 °C

11: 100 percent / Et₃N / CH₂Cl₂ / 3.5 h / 0 - 25 °C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; sodium periodate; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; lithium perchlorate; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 5: Swern oxidation;

DOI:10.1055/s-2002-33511

upstream raw materials:

methanesulfonyl chloride

(2R,3R)-2-Benzyloxy-3-((1S,2S)-2-benzyloxy-1-hydroxymethyl-pent-4-enyloxy)-hex-5-en-1-ol

allyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside

2,6-anhydro-7,8,9-trideoxy-D-glycero-L-galacto-non-8-enitol

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