((2S,3R,4R,5R,6S)-4-Benzyloxy-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-{2-[(1R,2S)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-1-methyl-propyl]-[1,3]dithian-2-yl}-methanone

Base Information

• Chemical Name: ((2S,3R,4R,5R,6S)-4-Benzyloxy-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-{2-[(1R,2S)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-1-methyl-propyl]-[1,3]dithian-2-yl}-methanone
• CAS No.: 92268-68-3
• Molecular Formula: C₃₀H₄₆O₇S₂
• Molecular Weight: 582.823

Synonyms:

Chemical Property of ((2S,3R,4R,5R,6S)-4-Benzyloxy-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-{2-[(1R,2S)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-1-methyl-propyl]-[1,3]dithian-2-yl}-methanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2S,3R,4R,5R,6S)-4-Benzyloxy-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-{2-[(1R,2S)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-1-methyl-propyl]-[1,3]dithian-2-yl}-methanone

There total 20 articles about ((2S,3R,4R,5R,6S)-4-Benzyloxy-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-{2-[(1R,2S)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-1-methyl-propyl]-[1,3]dithian-2-yl}-methanone 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:

methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-altro-pyranoside (19465-06-6) → ((2S,3R,4R,5R,6S)-4-Benzyloxy-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-{2-[(1R,2S)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-1-methyl-propyl]-[1,3]dithian-2-yl}-methanone (92268-68-3)

Guidance literature:

Multi-step reaction with 15 steps

1: 98 percent / Ac₂O / dimethylsulfoxide / Ambient temperature

2: 85 percent / NaOMe / methanol / 4 h / 0 °C

3: 96 percent / sodium borohydride / dimethylformamide; methanol / 1.5 h

4: 1.) NaH / 1.) DMF, 30 min; 2.) DMF, 0 deg C, 2 h; r.t.

5: 20percent Pd-C / ethyl acetate / 20 h

6: pyridine / 72 h / Ambient temperature

7: ethyldimethylaminopropyl carbodiimide hydrochloride / pyridine; dimethylsulfoxide; trifluoroacetic acid / 18 h / Ambient temperature

8: 80 percent / NaOMe / methanol / 27 h / -20 °C

9: 1.) sodium borohydride; 2.) AcOH / 1.) DMF, MeOH, 1 h; 2.) 0 deg C

10: 3.6 g / sulfuryl chloride / pyridine / Ambient temperature

11: tri-n-butyltin hydride, asobis-isobutyronitrile / toluene / 5 h / Heating

12: 1.) AcOH; 2.) sodium borohydride / 1.) water, 80 deg C, 2.5 h; 2.) EtOH, r.t., 2. 5h

13: 340 mg / BF₃-etherate / CH₂Cl₂ / 0 °C

14: 298 mg / champhosulfonic acid / benzene / 1 h / Ambient temperature

15: 1.) t-BuLi / 1.) hexane, -15 deg C, 1.5 h: 2.) ether, -78 deg C, 4 h

With sodium tetrahydroborate; sulfuryl dichloride; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tert.-butyl lithium; tri-n-butyl-tin hydride; sodium methylate; acetic anhydride; sodium hydride; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In pyridine; methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; trifluoroacetic acid; benzene;

DOI:10.1016/S0040-4020(01)82415-7

Reference yield:

Methyl 4,6-O-Benzylidene-2-deoxy-2-C-methyl-α-D-allopyranoside (75879-81-1) → ((2S,3R,4R,5R,6S)-4-Benzyloxy-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-{2-[(1R,2S)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-1-methyl-propyl]-[1,3]dithian-2-yl}-methanone (92268-68-3)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) NaH / 1.) DMF, 30 min; 2.) DMF, 0 deg C, 2 h; r.t.

2: 20percent Pd-C / ethyl acetate / 20 h

3: pyridine / 72 h / Ambient temperature

4: ethyldimethylaminopropyl carbodiimide hydrochloride / pyridine; dimethylsulfoxide; trifluoroacetic acid / 18 h / Ambient temperature

5: 80 percent / NaOMe / methanol / 27 h / -20 °C

6: 1.) sodium borohydride; 2.) AcOH / 1.) DMF, MeOH, 1 h; 2.) 0 deg C

7: 3.6 g / sulfuryl chloride / pyridine / Ambient temperature

8: tri-n-butyltin hydride, asobis-isobutyronitrile / toluene / 5 h / Heating

9: 1.) AcOH; 2.) sodium borohydride / 1.) water, 80 deg C, 2.5 h; 2.) EtOH, r.t., 2. 5h

10: 340 mg / BF₃-etherate / CH₂Cl₂ / 0 °C

11: 298 mg / champhosulfonic acid / benzene / 1 h / Ambient temperature

12: 1.) t-BuLi / 1.) hexane, -15 deg C, 1.5 h: 2.) ether, -78 deg C, 4 h

With sodium tetrahydroborate; sulfuryl dichloride; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tert.-butyl lithium; tri-n-butyl-tin hydride; sodium methylate; sodium hydride; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In pyridine; methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene; trifluoroacetic acid; benzene;

DOI:10.1016/S0040-4020(01)82415-7

Reference yield:

methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-arabino-hexopyranoside (64526-80-3) → ((2S,3R,4R,5R,6S)-4-Benzyloxy-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-{2-[(1R,2S)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-1-methyl-propyl]-[1,3]dithian-2-yl}-methanone (92268-68-3)

Guidance literature:

Multi-step reaction with 14 steps

1: 85 percent / NaOMe / methanol / 4 h / 0 °C

2: 96 percent / sodium borohydride / dimethylformamide; methanol / 1.5 h

3: 1.) NaH / 1.) DMF, 30 min; 2.) DMF, 0 deg C, 2 h; r.t.

4: 20percent Pd-C / ethyl acetate / 20 h

5: pyridine / 72 h / Ambient temperature

6: ethyldimethylaminopropyl carbodiimide hydrochloride / pyridine; dimethylsulfoxide; trifluoroacetic acid / 18 h / Ambient temperature

7: 80 percent / NaOMe / methanol / 27 h / -20 °C

8: 1.) sodium borohydride; 2.) AcOH / 1.) DMF, MeOH, 1 h; 2.) 0 deg C

9: 3.6 g / sulfuryl chloride / pyridine / Ambient temperature

10: tri-n-butyltin hydride, asobis-isobutyronitrile / toluene / 5 h / Heating

11: 1.) AcOH; 2.) sodium borohydride / 1.) water, 80 deg C, 2.5 h; 2.) EtOH, r.t., 2. 5h

12: 340 mg / BF₃-etherate / CH₂Cl₂ / 0 °C

13: 298 mg / champhosulfonic acid / benzene / 1 h / Ambient temperature

14: 1.) t-BuLi / 1.) hexane, -15 deg C, 1.5 h: 2.) ether, -78 deg C, 4 h

With sodium tetrahydroborate; sulfuryl dichloride; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tert.-butyl lithium; tri-n-butyl-tin hydride; sodium methylate; sodium hydride; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In pyridine; methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; trifluoroacetic acid; benzene;

DOI:10.1016/S0040-4020(01)82415-7

upstream raw materials:

2,4-dideoxy-2-C-methyl-3-O-methyl-5,6-O-isopropylidene-D-xylo-hexose propylenedithioacetal

methyl 6-aldehydo-3-O-benzyl-2,4-dideoxy-2,4-di-C-methyl-α-D-gulopyranoside

methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-altro-pyranoside

benzyl bromide

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