Chloro-methanesulfonic acid (2R,4S,5R)-5-((4R,5S)-4-allyl-2-phenyl-[1,3,2]dioxaborinan-5-yloxy)-2-phenyl-[1,3]dioxan-4-ylmethyl ester

Base Information

• Chemical Name: Chloro-methanesulfonic acid (2R,4S,5R)-5-((4R,5S)-4-allyl-2-phenyl-[1,3,2]dioxaborinan-5-yloxy)-2-phenyl-[1,3]dioxan-4-ylmethyl ester
• CAS No.: 475641-82-8
• Molecular Formula: C₂₄H₂₈BClO₈S
• Molecular Weight: 522.812

Synonyms:Chloro-methanesulfonic acid (2R,4S,5R)-5-((4R,5S)-4-allyl-2-phenyl-[1,3,2]dioxaborinan-5-yloxy)-2-phenyl-[1,3]dioxan-4-ylmethyl ester

Chemical Property of Chloro-methanesulfonic acid (2R,4S,5R)-5-((4R,5S)-4-allyl-2-phenyl-[1,3,2]dioxaborinan-5-yloxy)-2-phenyl-[1,3]dioxan-4-ylmethyl ester

Chemical Property:

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Technology Process of Chloro-methanesulfonic acid (2R,4S,5R)-5-((4R,5S)-4-allyl-2-phenyl-[1,3,2]dioxaborinan-5-yloxy)-2-phenyl-[1,3]dioxan-4-ylmethyl ester

There total 13 articles about Chloro-methanesulfonic acid (2R,4S,5R)-5-((4R,5S)-4-allyl-2-phenyl-[1,3,2]dioxaborinan-5-yloxy)-2-phenyl-[1,3]dioxan-4-ylmethyl 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: 98.0%

monochloromethanesulfonyl chloride (3518-65-8) + [(2R,4S,5R)-5-((4R,5S)-4-Allyl-2-phenyl-[1,3,2]dioxaborinan-5-yloxy)-2-phenyl-[1,3]dioxan-4-yl]-methanol (475641-72-6) → Chloro-methanesulfonic acid (2R,4S,5R)-5-((4R,5S)-4-allyl-2-phenyl-[1,3,2]dioxaborinan-5-yloxy)-2-phenyl-[1,3]dioxan-4-ylmethyl ester (475641-82-8)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 21 - 23 ℃;

DOI:10.1055/s-2002-33527

Reference yield:

((2R,3S,6S)-3-acetoxy-6-cyano-3,6-dihydro-2H-pyran-2-yl)methyl acetate (83938-00-5) → Chloro-methanesulfonic acid (2R,4S,5R)-5-((4R,5S)-4-allyl-2-phenyl-[1,3,2]dioxaborinan-5-yloxy)-2-phenyl-[1,3]dioxan-4-ylmethyl ester (475641-82-8)

Guidance literature:

Multi-step reaction with 12 steps

1: Amberlyst 15 / methanol / 24 h / Heating

2: Amberlyst 15 / CHCl₃ / 22.5 h

3: 100 percent / aq. OsO₄; NMO / dioxane / 96 h / 20 °C

4: 100 percent / 2,6-lutidine / CH₂Cl₂ / 72 h / 0 - 22 °C

5: DIBALH / CH₂Cl₂ / 0.2 h / -78 °C

6: aq. HCl / CH₂Cl₂ / 16 h / 22 °C

7: 79 percent / CH₂Cl₂ / 3.83 h / -78 - -20 °C

8: 95 percent / TBAF / tetrahydrofuran / 22 °C

9: aq. NaIO₄ / dioxane / 22 °C

10: NaBH₄ / methanol / 0 °C

11: 98 percent / benzene / Heating

12: 98 percent / 2,6-lutidine / CH₂Cl₂ / 21 - 23 °C

With 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; Amberlyst 15; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; benzene;

DOI:10.1055/s-2002-33527

Reference yield:

2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl cyanide (88180-36-3) → Chloro-methanesulfonic acid (2R,4S,5R)-5-((4R,5S)-4-allyl-2-phenyl-[1,3,2]dioxaborinan-5-yloxy)-2-phenyl-[1,3]dioxan-4-ylmethyl ester (475641-82-8)

Guidance literature:

Multi-step reaction with 11 steps

1: Amberlyst 15 / CHCl₃ / 22.5 h

2: 100 percent / aq. OsO₄; NMO / dioxane / 96 h / 20 °C

3: 100 percent / 2,6-lutidine / CH₂Cl₂ / 72 h / 0 - 22 °C

4: DIBALH / CH₂Cl₂ / 0.2 h / -78 °C

5: aq. HCl / CH₂Cl₂ / 16 h / 22 °C

6: 79 percent / CH₂Cl₂ / 3.83 h / -78 - -20 °C

7: 95 percent / TBAF / tetrahydrofuran / 22 °C

8: aq. NaIO₄ / dioxane / 22 °C

9: NaBH₄ / methanol / 0 °C

10: 98 percent / benzene / Heating

11: 98 percent / 2,6-lutidine / CH₂Cl₂ / 21 - 23 °C

With 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; Amberlyst 15; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; benzene;

DOI:10.1055/s-2002-33527

upstream raw materials:

monochloromethanesulfonyl chloride

[(2R,4S,5R)-5-((4R,5S)-4-Allyl-2-phenyl-[1,3,2]dioxaborinan-5-yloxy)-2-phenyl-[1,3]dioxan-4-yl]-methanol

((2R,3S,6S)-3-acetoxy-6-cyano-3,6-dihydro-2H-pyran-2-yl)methyl acetate

2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl cyanide

Downstream raw materials:

(Z)-(2R,4aR,6S,7R,11aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononene

{(2R,4S,5R)-5-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enyloxy]-2-phenyl-[1,3]dioxan-4-yl}-acetaldehyde

{(2R,4S,5R)-5-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enyloxy]-2-phenyl-[1,3]dioxan-4-yl}-acetonitrile

(2R,4S,5R)-4-Allyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enyloxy]-2-phenyl-[1,3]dioxane

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