(2R,3S)-1-Benzenesulfonyl-6-[1,3]dithian-2-yl-2-methyl-hexan-3-ol

Base Information

• Chemical Name: (2R,3S)-1-Benzenesulfonyl-6-[1,3]dithian-2-yl-2-methyl-hexan-3-ol
• CAS No.: 107172-27-0
• Molecular Formula: C₁₇H₂₆O₃S₃
• Molecular Weight: 374.59
• Mol file: 107172-27-0.mol

Synonyms:

Chemical Property of (2R,3S)-1-Benzenesulfonyl-6-[1,3]dithian-2-yl-2-methyl-hexan-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-1-Benzenesulfonyl-6-[1,3]dithian-2-yl-2-methyl-hexan-3-ol

There total 14 articles about (2R,3S)-1-Benzenesulfonyl-6-[1,3]dithian-2-yl-2-methyl-hexan-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:

tert-butyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside (69247-20-7,149279-18-5,23339-25-5) → (2R,3S)-1-Benzenesulfonyl-6-[1,3]dithian-2-yl-2-methyl-hexan-3-ol (107172-27-0,77890-90-5)

Guidance literature:

Multi-step reaction with 12 steps

1: H₂ / Pd-C(5percent) / ethyl acetate / 12 h

2: Et₃N, H₂O / methanol / Ambient temperature

3: CH₂Cl₂ / 0 deg C, then room temp., overnight

4: 86 percent / CSA / CH₂Cl₂ / 1.5 h / Ambient temperature

5: 93 percent / KOH, H₂O / methanol / 1.75 h

6: 78 percent / dipyridinium chromate / CH₂Cl₂ / 0.17 h / Ambient temperature

7: 30 percent / n-BuLi / methanol / -45 °C

8: 95 percent / MCPBA, aq.NaHCO₃(sat) / CH₂Cl₂ / 0 deg C, 1.5 h; room temp., 20 min

9: 1.) LiBr, 2.) KF / 1.) THF, -78 deg C; 2.) MeOH, room temp., 1.5 h

10: 1.) NaH; 2.) imidazole / 1.) THF,-20 deg C, 30 min, then 0 deg C, 15 min; 2.) 40 min

11: 38 percent / n-Bu₃SnH, AIBN / 0.33 h / 90 °C

12: ZnCl₂, HCl

With 1H-imidazole; hydrogenchloride; potassium fluoride; potassium hydroxide; n-butyllithium; pyridinium dichromate; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; water; hydrogen; tri-n-butyl-tin hydride; sodium hydride; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium bromide; zinc(II) chloride; 5%-palladium/activated carbon; In methanol; dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4020(01)90575-7

Reference yield:

D-glucal triacetate (2873-29-2) → (2R,3S)-1-Benzenesulfonyl-6-[1,3]dithian-2-yl-2-methyl-hexan-3-ol (107172-27-0,77890-90-5)

Guidance literature:

Multi-step reaction with 13 steps

1: 97 percent / BF₃-Et₂O / 1.67 h / Ambient temperature

2: H₂ / Pd-C(5percent) / ethyl acetate / 12 h

3: Et₃N, H₂O / methanol / Ambient temperature

4: CH₂Cl₂ / 0 deg C, then room temp., overnight

5: 86 percent / CSA / CH₂Cl₂ / 1.5 h / Ambient temperature

6: 93 percent / KOH, H₂O / methanol / 1.75 h

7: 78 percent / dipyridinium chromate / CH₂Cl₂ / 0.17 h / Ambient temperature

8: 30 percent / n-BuLi / methanol / -45 °C

9: 95 percent / MCPBA, aq.NaHCO₃(sat) / CH₂Cl₂ / 0 deg C, 1.5 h; room temp., 20 min

10: 1.) LiBr, 2.) KF / 1.) THF, -78 deg C; 2.) MeOH, room temp., 1.5 h

11: 1.) NaH; 2.) imidazole / 1.) THF,-20 deg C, 30 min, then 0 deg C, 15 min; 2.) 40 min

12: 38 percent / n-Bu₃SnH, AIBN / 0.33 h / 90 °C

13: ZnCl₂, HCl

With 1H-imidazole; hydrogenchloride; potassium fluoride; potassium hydroxide; n-butyllithium; pyridinium dichromate; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; boron trifluoride diethyl etherate; water; hydrogen; tri-n-butyl-tin hydride; sodium hydride; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium bromide; zinc(II) chloride; 5%-palladium/activated carbon; In methanol; dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4020(01)90575-7

Reference yield:

tert-butyl 2,3-deoxy-α-D-glucopyranoside (107108-67-8) → (2R,3S)-1-Benzenesulfonyl-6-[1,3]dithian-2-yl-2-methyl-hexan-3-ol (107172-27-0,77890-90-5)

Guidance literature:

Multi-step reaction with 10 steps

1: CH₂Cl₂ / 0 deg C, then room temp., overnight

2: 86 percent / CSA / CH₂Cl₂ / 1.5 h / Ambient temperature

3: 93 percent / KOH, H₂O / methanol / 1.75 h

4: 78 percent / dipyridinium chromate / CH₂Cl₂ / 0.17 h / Ambient temperature

5: 30 percent / n-BuLi / methanol / -45 °C

6: 95 percent / MCPBA, aq.NaHCO₃(sat) / CH₂Cl₂ / 0 deg C, 1.5 h; room temp., 20 min

7: 1.) LiBr, 2.) KF / 1.) THF, -78 deg C; 2.) MeOH, room temp., 1.5 h

8: 1.) NaH; 2.) imidazole / 1.) THF,-20 deg C, 30 min, then 0 deg C, 15 min; 2.) 40 min

9: 38 percent / n-Bu₃SnH, AIBN / 0.33 h / 90 °C

10: ZnCl₂, HCl

With 1H-imidazole; hydrogenchloride; potassium fluoride; potassium hydroxide; n-butyllithium; pyridinium dichromate; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; water; tri-n-butyl-tin hydride; sodium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; lithium bromide; zinc(II) chloride; In methanol; dichloromethane;

DOI:10.1016/S0040-4020(01)90575-7

upstream raw materials:

1.3-propanedithiol

(2S,6S)-2-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-6-methoxy-tetrahydro-pyran

(2S,6R)-2-((S)-2-Benzenesulfonyl-1-methyl-ethyl)-6-tert-butoxy-tetrahydro-pyran

tert-butyl 2,3-deoxy-α-D-glucopyranoside