(R)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-17-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-heptadecanoic acid tert-butyl ester

Base Information

Chemical Name:(R)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-17-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-heptadecanoic acid tert-butyl ester
CAS No.:628316-18-7
Molecular Formula:C₅₇H₇₆N₄O₉S
Molecular Weight:993.318
Hs Code.:

(R)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-17-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-heptadecanoic acid tert-butyl ester

Synonyms:(R)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-17-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-heptadecanoic acid tert-butyl ester

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Chemical Property of (R)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-17-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-heptadecanoic acid tert-butyl ester

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Technology Process of (R)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-17-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-heptadecanoic acid tert-butyl ester

There total 8 articles about (R)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-17-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-heptadecanoic acid tert-butyl 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: 85.0%

: 86-93-1
1-Phenyl-1H-tetrazole-5-thiol

: 404867-97-6
(3R)-tert-butyl [17-tert-butyldiphenylsilyloxy-3-(2,3,4-tri-O-benzyl-6-O-acetyl-β-D-glucopyranosyl)oxy]heptadecanoate

: 628316-18-7
(R)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-17-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-heptadecanoic acid tert-butyl ester

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; for 4h;
DOI:10.1021/ja036521e

Reference yield:

: 4356-77-8,35094-65-6,61277-56-3,65556-30-1,78185-13-4,78185-15-6,109958-31-8,109958-33-0,113532-02-8,59433-13-5
1,6-di-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose

: 628316-18-7
(R)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-17-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-heptadecanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 13.5 g / H₂NNH₂*AcOH / dimethylformamide / 5 h / 20 °C

2: 74 percent / NaH / CH₂Cl₂ / 2 h

3: 62 percent / 4A molecular sieves; BF₃*Et₂O / CH₂Cl₂ / 2 h / -40 °C

4: 85 percent / PPh₃; diisopropylazodicarboxylate / tetrahydrofuran / 4 h

With di-isopropyl azodicarboxylate; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrazinium monoacetate; sodium hydride; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 4: Mitsunobu reaction;
DOI:10.1021/ja036521e

Reference yield:

: 106-02-5,81031-90-5
pentadecanolide

: 628316-18-7
(R)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-17-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-heptadecanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: LDA / hexane; tetrahydrofuran / 1 h / -78 °C

1.2: hexane; tetrahydrofuran / 2 h / -40 °C

1.3: 3.1 g / H₂; [RuCl₂(COD)]n; Et₃N / (R)-BINAP / methanol; tetrahydrofuran / 15 h / 70 °C / 11400 Torr

2.1: 81 percent / imidazole / dimethylformamide / 4 h / 20 °C

3.1: 62 percent / 4A molecular sieves; BF₃*Et₂O / CH₂Cl₂ / 2 h / -40 °C

4.1: 85 percent / PPh₃; diisopropylazodicarboxylate / tetrahydrofuran / 4 h

With 1H-imidazole; di-isopropyl azodicarboxylate; 4 A molecular sieve; boron trifluoride diethyl etherate; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 4.1: Mitsunobu reaction;
DOI:10.1021/ja036521e