(3R,4R,5S,7S,13R,14S,16S)-17-Azido-4,13,14,16-tetrakis-benzyloxy-3,7-dimethyl-heptadec-9-yn-5-ol

Base Information

Chemical Name:(3R,4R,5S,7S,13R,14S,16S)-17-Azido-4,13,14,16-tetrakis-benzyloxy-3,7-dimethyl-heptadec-9-yn-5-ol
CAS No.:251353-65-8
Molecular Formula:C₄₇H₅₉N₃O₅
Molecular Weight:746.003
Hs Code.:

Synonyms:(3R,4R,5S,7S,13R,14S,16S)-17-Azido-4,13,14,16-tetrakis-benzyloxy-3,7-dimethyl-heptadec-9-yn-5-ol

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Chemical Property of (3R,4R,5S,7S,13R,14S,16S)-17-Azido-4,13,14,16-tetrakis-benzyloxy-3,7-dimethyl-heptadec-9-yn-5-ol

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Technology Process of (3R,4R,5S,7S,13R,14S,16S)-17-Azido-4,13,14,16-tetrakis-benzyloxy-3,7-dimethyl-heptadec-9-yn-5-ol

There total 20 articles about (3R,4R,5S,7S,13R,14S,16S)-17-Azido-4,13,14,16-tetrakis-benzyloxy-3,7-dimethyl-heptadec-9-yn-5-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: 69.0%

: 251353-64-7
(2S,4S,5R,11S,13S,14R,15R)-2,4,5,14-Tetrakis-benzyloxy-11,15-dimethyl-heptadec-8-yne-1,13-diol

: 251353-65-8
(3R,4R,5S,7S,13R,14S,16S)-17-Azido-4,13,14,16-tetrakis-benzyloxy-3,7-dimethyl-heptadec-9-yn-5-ol

Guidance literature:: With tris-(2-chloro-ethyl)-amine; triphenylphosphine; diethylazodicarboxylate; In toluene;
DOI:10.1016/S0040-4039(99)01322-2

Reference yield:

: (2S,3R)-3-Benzyloxy-2-methyl-3-((S)-5-oxo-tetrahydro-furan-2-yl)-propionaldehyde

: 251353-65-8
(3R,4R,5S,7S,13R,14S,16S)-17-Azido-4,13,14,16-tetrakis-benzyloxy-3,7-dimethyl-heptadec-9-yn-5-ol

Guidance literature:: Multi-step reaction with 11 steps

1: n-BuLi / tetrahydrofuran

2: H₂ / Pd-C / ethyl acetate

3: TfOH / CH₂Cl₂; cyclohexane

4: 68 percent / LiHMDS / tetrahydrofuran / -78 °C

5: 72 percent / n-BuLi / diethyl ether / -20 °C

6: 85 percent / NaBH₄; CeCl₃ / methanol

7: 97 percent / Ac₂O; Py

8: 84 percent / Pd(OAc)2; n-Bu₃P / tetrahydrofuran

9: LiAlH₄ / tetrahydrofuran

10: PPTS / ethanol

11: 69 percent / HN₃; Ph₃P; DEAD / toluene

With pyridine; palladium diacetate; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; cerium(III) chloride; tributylphosphine; tris-(2-chloro-ethyl)-amine; trifluorormethanesulfonic acid; hydrogen; pyridinium p-toluenesulfonate; acetic anhydride; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; cyclohexane; ethyl acetate; toluene; 1: Condensation / 2: Catalytic hydrogenation / 3: Etherification / 4: Alkylation / 5: Acylation / 6: Reduction / 7: Esterification / 8: deoxygenation / 9: Reduction / 10: ether cleavage / 11: Alkylation;
DOI:10.1016/S0040-4039(99)01322-2

Reference yield:

: 251353-58-9
(S)-5-((1R,2R)-1-Benzyloxy-2-methyl-but-3-enyl)-dihydro-furan-2-one

: 251353-65-8
(3R,4R,5S,7S,13R,14S,16S)-17-Azido-4,13,14,16-tetrakis-benzyloxy-3,7-dimethyl-heptadec-9-yn-5-ol

Guidance literature:: Multi-step reaction with 10 steps

1: H₂ / Pd-C / ethyl acetate

2: TfOH / CH₂Cl₂; cyclohexane

3: 68 percent / LiHMDS / tetrahydrofuran / -78 °C

4: 72 percent / n-BuLi / diethyl ether / -20 °C

5: 85 percent / NaBH₄; CeCl₃ / methanol

6: 97 percent / Ac₂O; Py

7: 84 percent / Pd(OAc)2; n-Bu₃P / tetrahydrofuran

8: LiAlH₄ / tetrahydrofuran

9: PPTS / ethanol

10: 69 percent / HN₃; Ph₃P; DEAD / toluene

With pyridine; palladium diacetate; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; cerium(III) chloride; tributylphosphine; tris-(2-chloro-ethyl)-amine; trifluorormethanesulfonic acid; hydrogen; pyridinium p-toluenesulfonate; acetic anhydride; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; cyclohexane; ethyl acetate; toluene; 1: Catalytic hydrogenation / 2: Etherification / 3: Alkylation / 4: Acylation / 5: Reduction / 6: Esterification / 7: deoxygenation / 8: Reduction / 9: ether cleavage / 10: Alkylation;
DOI:10.1016/S0040-4039(99)01322-2