(S)-1-benzyloxy-2-[(tert-butyldiphenylsilyloxy)methyl]-6-N-(p-toluenesulfonyl)-6-aza-3,9-dioxa-11-undecanol

Base Information

• Chemical Name: (S)-1-benzyloxy-2-[(tert-butyldiphenylsilyloxy)methyl]-6-N-(p-toluenesulfonyl)-6-aza-3,9-dioxa-11-undecanol
• CAS No.: 307532-35-0
• Molecular Formula: C₃₉H₅₁NO₇SSi
• Molecular Weight: 705.988
• Mol file: 307532-35-0.mol

Synonyms:(S)-1-benzyloxy-2-[(tert-butyldiphenylsilyloxy)methyl]-6-N-(p-toluenesulfonyl)-6-aza-3,9-dioxa-11-undecanol

Chemical Property of (S)-1-benzyloxy-2-[(tert-butyldiphenylsilyloxy)methyl]-6-N-(p-toluenesulfonyl)-6-aza-3,9-dioxa-11-undecanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-benzyloxy-2-[(tert-butyldiphenylsilyloxy)methyl]-6-N-(p-toluenesulfonyl)-6-aza-3,9-dioxa-11-undecanol

There total 7 articles about (S)-1-benzyloxy-2-[(tert-butyldiphenylsilyloxy)methyl]-6-N-(p-toluenesulfonyl)-6-aza-3,9-dioxa-11-undecanol 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: 65.0%

N-<2-(2-hydroxyethoxy)ethyl>-4-methylbenzenesulfonamide (783-88-0) + (S)-1-O-benzyl-3-O-tert-butyldiphenylsilyl-2-O-[2-(p-toluenesulfonyloxy)ethyl]glycerol (307532-34-9) → (S)-1-benzyloxy-2-[(tert-butyldiphenylsilyloxy)methyl]-6-N-(p-toluenesulfonyl)-6-aza-3,9-dioxa-11-undecanol (307532-35-0)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide;

DOI:10.1081/SCC-120004151

Reference yield:

(S)-1-O-benzyl-3-O-(tert-butyldiphenylsilyl)-2-O-(2-hydroxyethyl)glycerol (261959-92-6) → (S)-1-benzyloxy-2-[(tert-butyldiphenylsilyloxy)methyl]-6-N-(p-toluenesulfonyl)-6-aza-3,9-dioxa-11-undecanol (307532-35-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / pyridine

2: 65 percent / K₂CO₃ / dimethylformamide

With pyridine; potassium carbonate; In N,N-dimethyl-formamide;

DOI:10.1081/SCC-120004151

Reference yield:

(R)-3-benzyloxy-1,2-propanediol (56552-80-8) → (S)-1-benzyloxy-2-[(tert-butyldiphenylsilyloxy)methyl]-6-N-(p-toluenesulfonyl)-6-aza-3,9-dioxa-11-undecanol (307532-35-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 88 percent / imidazole / dimethylformamide

2.1: NaH / tetrahydrofuran / 45 h

2.2: 93 percent / tetrahydrofuran / 4 h

3.1: OsO₄; N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H₂O; tetrahydrofuran / 24 h / 20 °C

3.2: Pb(OAc)4 / tetrahydrofuran / 1 h

3.3: 81 percent / NaBH₄; NaOH / tetrahydrofuran; H₂O / 2 h / 0 - 20 °C

4.1: 87 percent / pyridine / 16 h / 0 - 5 °C

5.1: 65 percent / K₂CO₃ / dimethylformamide / 48 h / Heating

With pyridine; 1H-imidazole; osmium(VIII) oxide; sodium hydride; potassium carbonate; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Substitution / 2.1: Etherification / 2.2: Substitution / 3.1: Dihydroxylation / 3.2: Elimination / 3.3: Reduction / 4.1: Tosylation / 5.1: Substitution;

DOI:10.1021/jo000766h

upstream raw materials:

N-<2-(2-hydroxyethoxy)ethyl>-4-methylbenzenesulfonamide

(S)-1-O-benzyl-3-O-tert-butyldiphenylsilyl-2-O-[2-(p-toluenesulfonyloxy)ethyl]glycerol

(S)-1-O-benzyl-3-O-(tert-butyldiphenylsilyl)-2-O-(2-hydroxyethyl)glycerol

(R)-3-benzyloxy-1,2-propanediol

Downstream raw materials:

(S)-2-[(tert-butyldiphenylsilyloxy)methyl]-6-N-(p-toluenesulfonyl)-6-aza-3,9-dioxa-1,11-undecanediol

(R)-1,11-bis(methanesulfonyloxy)-2-[(tert-butyldiphenylsilyloxy)methyl]-6-N-(p-toluenesulfonyl)-6-aza-3,9-dioxaundecane

(S)-2-[(tert-butyldiphenylsilyloxy)methyl]-4,10,16-tris(p-toluenesulfonyl)-4,10,16-triaza-1,7,13-trioxacyclooctadecane