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

Base Information

Chemical Name:(2S,4S,5R,11S,13S,14R,15R)-2,4,5,14-Tetrakis-benzyloxy-11,15-dimethyl-heptadec-8-yne-1,13-diol
CAS No.:251353-64-7
Molecular Formula:C₄₇H₆₀O₆
Molecular Weight:720.99
Hs Code.:

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

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Chemical Property of (2S,4S,5R,11S,13S,14R,15R)-2,4,5,14-Tetrakis-benzyloxy-11,15-dimethyl-heptadec-8-yne-1,13-diol

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Technology Process of (2S,4S,5R,11S,13S,14R,15R)-2,4,5,14-Tetrakis-benzyloxy-11,15-dimethyl-heptadec-8-yne-1,13-diol

There total 19 articles about (2S,4S,5R,11S,13S,14R,15R)-2,4,5,14-Tetrakis-benzyloxy-11,15-dimethyl-heptadec-8-yne-1,13-diol 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:

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

: 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

Guidance literature:: Multi-step reaction with 10 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

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

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

Guidance literature:: Multi-step reaction with 9 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

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

Reference yield:

: 251353-68-1
(S)-5-((1R,2R)-1-Benzyloxy-3-hydroxy-2-methyl-propyl)-dihydro-furan-2-one

: 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

Guidance literature:: Multi-step reaction with 11 steps

2: n-BuLi / tetrahydrofuran

3: H₂ / Pd-C / ethyl acetate

4: TfOH / CH₂Cl₂; cyclohexane

5: 68 percent / LiHMDS / tetrahydrofuran / -78 °C

6: 72 percent / n-BuLi / diethyl ether / -20 °C

7: 85 percent / NaBH₄; CeCl₃ / methanol

8: 97 percent / Ac₂O; Py

9: 84 percent / Pd(OAc)2; n-Bu₃P / tetrahydrofuran

10: LiAlH₄ / tetrahydrofuran

11: PPTS / ethanol

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