(2S,3S,6R)-5-Benzenesulfonyl-2-{2-[(4R,5S,6R)-6-isopropyl-5-methoxy-2-(4-methoxy-phenyl)-[1,3]dioxan-4-ylmethyl]-[1,3]dithian-2-yl}-6-((2S,3R,6S)-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-heptan-3-ol

Base Information

• Chemical Name: (2S,3S,6R)-5-Benzenesulfonyl-2-{2-[(4R,5S,6R)-6-isopropyl-5-methoxy-2-(4-methoxy-phenyl)-[1,3]dioxan-4-ylmethyl]-[1,3]dithian-2-yl}-6-((2S,3R,6S)-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-heptan-3-ol
• CAS No.: 193475-38-6
• Molecular Formula: C₄₃H₆₄O₉S₃
• Molecular Weight: 821.174
• Mol file: 193475-38-6.mol

Synonyms:

Chemical Property of (2S,3S,6R)-5-Benzenesulfonyl-2-{2-[(4R,5S,6R)-6-isopropyl-5-methoxy-2-(4-methoxy-phenyl)-[1,3]dioxan-4-ylmethyl]-[1,3]dithian-2-yl}-6-((2S,3R,6S)-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-heptan-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,6R)-5-Benzenesulfonyl-2-{2-[(4R,5S,6R)-6-isopropyl-5-methoxy-2-(4-methoxy-phenyl)-[1,3]dioxan-4-ylmethyl]-[1,3]dithian-2-yl}-6-((2S,3R,6S)-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-heptan-3-ol

There total 17 articles about (2S,3S,6R)-5-Benzenesulfonyl-2-{2-[(4R,5S,6R)-6-isopropyl-5-methoxy-2-(4-methoxy-phenyl)-[1,3]dioxan-4-ylmethyl]-[1,3]dithian-2-yl}-6-((2S,3R,6S)-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-heptan-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:

phenylthioethynyl trimethylsilane (63139-23-1) → (2S,3S,6R)-5-Benzenesulfonyl-2-{2-[(4R,5S,6R)-6-isopropyl-5-methoxy-2-(4-methoxy-phenyl)-[1,3]dioxan-4-ylmethyl]-[1,3]dithian-2-yl}-6-((2S,3R,6S)-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-heptan-3-ol (193475-38-6)

Guidance literature:

Multi-step reaction with 14 steps

1: 61 percent / BF₃*OEt₂ / acetonitrile

2: 88 percent / Na₂PtCl₆

3: 96 percent / MCPBA, Na₂HPO₄

4: tetrahydrofuran / -78 °C

5: TBAF / tetrahydrofuran

6: 95 percent / (PhO)3PMeI / benzene

7: 94 percent / Zn / pyridine; ethanol

8: 93 percent / i-Pr₂NEt

9: 1.) OsO₄, NMO, 2.) NaIO₄ / 2.) THF, H₂O

10: n-BuLi / tetrahydrofuran

11: PCC, 4 Angstroem molecular sieves

12: H₂ / 10percent Pd-C

13: TsOH / methanol / Heating

14: n-BuLi, BF₃*OEt₂ / -78 °C

With sodium hexachloroplatinate; sodium periodate; disodium hydrogenphosphate; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; methyltriphenoxyphosphonium iodide; hydrogen; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; zinc; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; acetonitrile; benzene;

DOI:10.1055/s-1997-3257

Reference yield:

isopropyl 2,4,6-tri-O-acetyl-3-deoxy-α-D-erythro-hex-2-enopyranoside (93662-86-3) → (2S,3S,6R)-5-Benzenesulfonyl-2-{2-[(4R,5S,6R)-6-isopropyl-5-methoxy-2-(4-methoxy-phenyl)-[1,3]dioxan-4-ylmethyl]-[1,3]dithian-2-yl}-6-((2S,3R,6S)-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-heptan-3-ol (193475-38-6)

Guidance literature:

Multi-step reaction with 17 steps

1: 79 percent / tetrahydrofuran

2: H₂ / 10percent Pd-C

3: imidazole / dimethylformamide

4: 61 percent / BF₃*OEt₂ / acetonitrile

5: 88 percent / Na₂PtCl₆

6: 96 percent / MCPBA, Na₂HPO₄

7: tetrahydrofuran / -78 °C

8: TBAF / tetrahydrofuran

9: 95 percent / (PhO)3PMeI / benzene

10: 94 percent / Zn / pyridine; ethanol

11: 93 percent / i-Pr₂NEt

12: 1.) OsO₄, NMO, 2.) NaIO₄ / 2.) THF, H₂O

13: n-BuLi / tetrahydrofuran

14: PCC, 4 Angstroem molecular sieves

15: H₂ / 10percent Pd-C

16: TsOH / methanol / Heating

17: n-BuLi, BF₃*OEt₂ / -78 °C

With 1H-imidazole; sodium hexachloroplatinate; sodium periodate; disodium hydrogenphosphate; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; methyltriphenoxyphosphonium iodide; hydrogen; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; zinc; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1055/s-1997-3257

Reference yield:

((2S,6S)-6-Isopropoxy-5-methylene-5,6-dihydro-2H-pyran-2-yl)-methanol (193475-27-3) → (2S,3S,6R)-5-Benzenesulfonyl-2-{2-[(4R,5S,6R)-6-isopropyl-5-methoxy-2-(4-methoxy-phenyl)-[1,3]dioxan-4-ylmethyl]-[1,3]dithian-2-yl}-6-((2S,3R,6S)-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-heptan-3-ol (193475-38-6)

Guidance literature:

Multi-step reaction with 16 steps

1: H₂ / 10percent Pd-C

2: imidazole / dimethylformamide

3: 61 percent / BF₃*OEt₂ / acetonitrile

4: 88 percent / Na₂PtCl₆

5: 96 percent / MCPBA, Na₂HPO₄

6: tetrahydrofuran / -78 °C

7: TBAF / tetrahydrofuran

8: 95 percent / (PhO)3PMeI / benzene

9: 94 percent / Zn / pyridine; ethanol

10: 93 percent / i-Pr₂NEt

11: 1.) OsO₄, NMO, 2.) NaIO₄ / 2.) THF, H₂O

12: n-BuLi / tetrahydrofuran

13: PCC, 4 Angstroem molecular sieves

14: H₂ / 10percent Pd-C

15: TsOH / methanol / Heating

16: n-BuLi, BF₃*OEt₂ / -78 °C

With 1H-imidazole; sodium hexachloroplatinate; sodium periodate; disodium hydrogenphosphate; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; methyltriphenoxyphosphonium iodide; hydrogen; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; zinc; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1055/s-1997-3257

upstream raw materials:

phenylthioethynyl trimethylsilane

isopropyl 2,4,6-tri-O-acetyl-3-deoxy-α-D-erythro-hex-2-enopyranoside

((2S,6S)-6-Isopropoxy-5-methylene-5,6-dihydro-2H-pyran-2-yl)-methanol

(2R,3S,4R)-1-Benzenesulfonyl-2,4-dimethyl-oct-7-en-3-ol

Downstream raw materials:

(2S,3S,6S)-2-{2-[(4R,5S,6R)-6-Isopropyl-5-methoxy-2-(4-methoxy-phenyl)-[1,3]dioxan-4-ylmethyl]-[1,3]dithian-2-yl}-6-((2R,3R,6S)-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-heptan-3-ol