Methanesulfonic acid (4aR,6R,7S,8S,8aR)-8-benzyloxy-2,2-dimethyl-6-tritylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Base Information

• Chemical Name: Methanesulfonic acid (4aR,6R,7S,8S,8aR)-8-benzyloxy-2,2-dimethyl-6-tritylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester
• CAS No.: 616238-34-7
• Molecular Formula: C₃₆H₃₈O₇S₂
• Molecular Weight: 646.826
• Mol file: 616238-34-7.mol

Synonyms:Methanesulfonic acid (4aR,6R,7S,8S,8aR)-8-benzyloxy-2,2-dimethyl-6-tritylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Chemical Property of Methanesulfonic acid (4aR,6R,7S,8S,8aR)-8-benzyloxy-2,2-dimethyl-6-tritylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid (4aR,6R,7S,8S,8aR)-8-benzyloxy-2,2-dimethyl-6-tritylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

There total 6 articles about Methanesulfonic acid (4aR,6R,7S,8S,8aR)-8-benzyloxy-2,2-dimethyl-6-tritylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl 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:

methanesulfonyl chloride (124-63-0) + (4aR,6R,7S,8R,8aR)-8-Benzyloxy-2,2-dimethyl-6-tritylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (616238-33-6) → Methanesulfonic acid (4aR,6R,7S,8S,8aR)-8-benzyloxy-2,2-dimethyl-6-tritylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (616238-34-7)

Guidance literature:

With dmap; In pyridine; at 20 ℃;

DOI:10.1021/ol0353518

Reference yield:

triphenylmethanethiol (3695-77-0) → Methanesulfonic acid (4aR,6R,7S,8S,8aR)-8-benzyloxy-2,2-dimethyl-6-tritylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (616238-34-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: BF₃*Et₂O / nitromethane / 20 °C

2.1: NaOMe / methanol / 20 °C

3.1: 74 percent / pTSA / dimethylformamide / 1 h / 0 °C

4.1: Bu₂SnO / Heating

4.2: 67 percent / dimethylformamide / 20 °C

5.1: DMAP / pyridine / 20 °C

With dmap; boron trifluoride diethyl etherate; sodium methylate; di(n-butyl)tin oxide; toluene-4-sulfonic acid; In pyridine; methanol; nitromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol0353518

Reference yield:

triphenylmethyl 1-thio-α-D-mannopyranoside (616238-31-4) → Methanesulfonic acid (4aR,6R,7S,8S,8aR)-8-benzyloxy-2,2-dimethyl-6-tritylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (616238-34-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 74 percent / pTSA / dimethylformamide / 1 h / 0 °C

2.1: Bu₂SnO / Heating

2.2: 67 percent / dimethylformamide / 20 °C

3.1: DMAP / pyridine / 20 °C

With dmap; di(n-butyl)tin oxide; toluene-4-sulfonic acid; In pyridine; N,N-dimethyl-formamide;

DOI:10.1021/ol0353518

upstream raw materials:

methanesulfonyl chloride

(4aR,6R,7S,8R,8aR)-8-Benzyloxy-2,2-dimethyl-6-tritylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

triphenylmethanethiol

triphenylmethyl 1-thio-α-D-mannopyranoside

Downstream raw materials:

methyl 3-O-benzyl-4,6-O-isopropylidene-2-deoxy-2-thio-2-S-trityl-β-D-glucopyranoside