(2S,3R,7Z)-2-azido-3-[(tert-butyl)dimethylsilyloxy]-1-{6-O-[(tert-butyl)diphenylsilyl]-3,4-O-isopropylidene-2-O-(trimethylacetyl)-β-D-galactopyranosyloxy}-12-[(1R,2S)-2-decylcyclopropyl]dodec-7-ene

Base Information

• Chemical Name: (2S,3R,7Z)-2-azido-3-[(tert-butyl)dimethylsilyloxy]-1-{6-O-[(tert-butyl)diphenylsilyl]-3,4-O-isopropylidene-2-O-(trimethylacetyl)-β-D-galactopyranosyloxy}-12-[(1R,2S)-2-decylcyclopropyl]dodec-7-ene
• CAS No.: 304856-95-9
• Molecular Formula: C₆₁H₁₀₁N₃O₈Si₂
• Molecular Weight: 1060.66

Synonyms:(2S,3R,7Z)-2-azido-3-[(tert-butyl)dimethylsilyloxy]-1-{6-O-[(tert-butyl)diphenylsilyl]-3,4-O-isopropylidene-2-O-(trimethylacetyl)-β-D-galactopyranosyloxy}-12-[(1R,2S)-2-decylcyclopropyl]dodec-7-ene

Chemical Property of (2S,3R,7Z)-2-azido-3-[(tert-butyl)dimethylsilyloxy]-1-{6-O-[(tert-butyl)diphenylsilyl]-3,4-O-isopropylidene-2-O-(trimethylacetyl)-β-D-galactopyranosyloxy}-12-[(1R,2S)-2-decylcyclopropyl]dodec-7-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,7Z)-2-azido-3-[(tert-butyl)dimethylsilyloxy]-1-{6-O-[(tert-butyl)diphenylsilyl]-3,4-O-isopropylidene-2-O-(trimethylacetyl)-β-D-galactopyranosyloxy}-12-[(1R,2S)-2-decylcyclopropyl]dodec-7-ene

There total 17 articles about (2S,3R,7Z)-2-azido-3-[(tert-butyl)dimethylsilyloxy]-1-{6-O-[(tert-butyl)diphenylsilyl]-3,4-O-isopropylidene-2-O-(trimethylacetyl)-β-D-galactopyranosyloxy}-12-[(1R,2S)-2-decylcyclopropyl]dodec-7-ene 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: 98.0%

6-O-[(tert-butyl)diphenylsilyl]-3,4-O-isopropylidene-2-O-(trimethylacetyl)-D-galactopyranosyl fluoride + (2S,3R,7Z)-2-azido-3-[(tert-butyl)dimethylsilyloxy]-12-[(1R,2S)-2-decylcyclopropyl]dodec-7-en-1-ol (304856-62-0) → (2S,3R,7Z)-2-azido-3-[(tert-butyl)dimethylsilyloxy]-1-{6-O-[(tert-butyl)diphenylsilyl]-3,4-O-isopropylidene-2-O-(trimethylacetyl)-β-D-galactopyranosyloxy}-12-[(1R,2S)-2-decylcyclopropyl]dodec-7-ene (304856-95-9)

Guidance literature:

With 2,6-di-tert-butyl-4-methylpyridine; silver trifluoromethanesulfonate; tin(ll) chloride; In dichloromethane; at 0 - 25 ℃; for 6.5h;

DOI:10.1002/1522-2675(20000809)83:8<1977::AID-HLCA1977>3.0.CO;2-D

Reference yield:

tridec-2-yn-1-ol (51887-25-3) → (2S,3R,7Z)-2-azido-3-[(tert-butyl)dimethylsilyloxy]-1-{6-O-[(tert-butyl)diphenylsilyl]-3,4-O-isopropylidene-2-O-(trimethylacetyl)-β-D-galactopyranosyloxy}-12-[(1R,2S)-2-decylcyclopropyl]dodec-7-ene (304856-95-9)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 96 percent / H₂ / Pd/BaSO₄ / pyridine / 10 h / 25 °C / 760 Torr

2.1: Zn(CH₂I)2*DME / CH₂Cl₂ / 6 h / -15 - 25 °C

3.1: 96 percent / I₂; imidazole; Ph₃P / acetonitrile; diethyl ether / 1 h / 0 °C

4.1: Mg / tetrahydrofuran

4.2: 84 percent / Li₂CuCl₂ / tetrahydrofuran / 0.5 h / 0 °C

5.1: 100 percent / PPTS / methanol / 5 h / 55 °C

6.1: 97 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 25 °C

7.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.25 h / 0 °C

7.2: 97 percent / tetrahydrofuran / 0.75 h / 0 °C

8.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 0 - 25 °C

8.2: 84 percent / H₂O₂; NaHCO₃; H₂O / tetrahydrofuran / 1.5 h / 25 °C

9.1: 97 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 25 °C

10.1: NaH / tetrahydrofuran / 0.25 h / 0 °C

10.2: 96 percent / tetrahydrofuran / 0.5 h / -78 °C

11.1: 98 percent / AD-mix β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 8 h / 0 °C

12.1: 100 percent / H₂ / Lindlar catalyst / ethanol / 0.67 h / 25 °C / 760 Torr

13.1: 84 percent / pyridine / 6.5 h / 0 °C

14.1: 95 percent / NaN₃ / dimethylformamide / 36 h / 25 °C

15.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / -78 - 25 °C

16.1: 92 percent / LiBH₄ / tetrahydrofuran / 10 h / 0 °C

17.1: 98 percent / SnCl₂; AgOTf; 2,6-di(tert-butyl)-4-methylpyridine / CH₂Cl₂ / 6.5 h / 0 - 25 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; lithium borohydride; sodium azide; 2,6-di-tert-butyl-4-methylpyridine; oxalyl dichloride; methanesulfonamide; hydrogen; iodine; silver trifluoromethanesulfonate; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydride; magnesium; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; (ICH₂)2Zn dimethoxyethane complex; tin(ll) chloride; Pd-BaSO₄; Lindlar's catalyst; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 1.1: Catalytic hydrogenation / 2.1: cyclopropanation / 3.1: Iodination / 4.1: Metallation / 4.2: Grignard reaction / 5.1: ether cleavage / 6.1: Swern oxidation / 7.1: deprotonation / 7.2: Wittig olefination / 8.1: hydroboration / 8.2: Oxidation / 9.1: Swern oxidation / 10.1: Metallation / 10.2: olefination / 11.1: Sharpless asymmetric dihydroxylation / 12.1: Catalytic hydrogenation / 13.1: Esterification / 14.1: Substitution / 15.1: silylation / 16.1: Reduction / 17.1: glycosidation;

DOI:10.1002/1522-2675(20000809)83:8<1977::AID-HLCA1977>3.0.CO;2-D

Reference yield:

(Z)-tridec-2-en-1-ols (74962-99-5,68480-25-1) → (2S,3R,7Z)-2-azido-3-[(tert-butyl)dimethylsilyloxy]-1-{6-O-[(tert-butyl)diphenylsilyl]-3,4-O-isopropylidene-2-O-(trimethylacetyl)-β-D-galactopyranosyloxy}-12-[(1R,2S)-2-decylcyclopropyl]dodec-7-ene (304856-95-9)

Guidance literature:

Multi-step reaction with 16 steps

1.1: Zn(CH₂I)2*DME / CH₂Cl₂ / 6 h / -15 - 25 °C

2.1: 96 percent / I₂; imidazole; Ph₃P / acetonitrile; diethyl ether / 1 h / 0 °C

3.1: Mg / tetrahydrofuran

3.2: 84 percent / Li₂CuCl₂ / tetrahydrofuran / 0.5 h / 0 °C

4.1: 100 percent / PPTS / methanol / 5 h / 55 °C

5.1: 97 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 25 °C

6.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.25 h / 0 °C

6.2: 97 percent / tetrahydrofuran / 0.75 h / 0 °C

7.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 0 - 25 °C

7.2: 84 percent / H₂O₂; NaHCO₃; H₂O / tetrahydrofuran / 1.5 h / 25 °C

8.1: 97 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 25 °C

9.1: NaH / tetrahydrofuran / 0.25 h / 0 °C

9.2: 96 percent / tetrahydrofuran / 0.5 h / -78 °C

10.1: 98 percent / AD-mix β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 8 h / 0 °C

11.1: 100 percent / H₂ / Lindlar catalyst / ethanol / 0.67 h / 25 °C / 760 Torr

12.1: 84 percent / pyridine / 6.5 h / 0 °C

13.1: 95 percent / NaN₃ / dimethylformamide / 36 h / 25 °C

14.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / -78 - 25 °C

15.1: 92 percent / LiBH₄ / tetrahydrofuran / 10 h / 0 °C

16.1: 98 percent / SnCl₂; AgOTf; 2,6-di(tert-butyl)-4-methylpyridine / CH₂Cl₂ / 6.5 h / 0 - 25 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; lithium borohydride; sodium azide; 2,6-di-tert-butyl-4-methylpyridine; oxalyl dichloride; methanesulfonamide; hydrogen; iodine; silver trifluoromethanesulfonate; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydride; magnesium; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; (ICH₂)2Zn dimethoxyethane complex; tin(ll) chloride; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 1.1: cyclopropanation / 2.1: Iodination / 3.1: Metallation / 3.2: Grignard reaction / 4.1: ether cleavage / 5.1: Swern oxidation / 6.1: deprotonation / 6.2: Wittig olefination / 7.1: hydroboration / 7.2: Oxidation / 8.1: Swern oxidation / 9.1: Metallation / 9.2: olefination / 10.1: Sharpless asymmetric dihydroxylation / 11.1: Catalytic hydrogenation / 12.1: Esterification / 13.1: Substitution / 14.1: silylation / 15.1: Reduction / 16.1: glycosidation;

DOI:10.1002/1522-2675(20000809)83:8<1977::AID-HLCA1977>3.0.CO;2-D

upstream raw materials:

(2S,3R,7Z)-2-azido-3-[(tert-butyl)dimethylsilyloxy]-12-[(1R,2S)-2-decylcyclopropyl]dodec-7-en-1-ol

tridec-2-yn-1-ol

(Z)-tridec-2-en-1-ols

[(1R,2S)-2-decylcylopropyl]methanol

Downstream raw materials:

C₈₄H₁₄₃NO₉Si₂

(2S,3R,7Z)-2-azido-3-[(tert-butyl)dimethylsilyloxy]-1-{6-O-[(tert-butyl)diphenylsilyl]-3,4-O-isopropylidene-2-O-(3-methylbut-2-enyl)-β-D-galactopyranosyloxy}-12-[(1R,2S)-2-decylcyclopropyl]dec-7-ene

(2S,3R,7Z)-2-amino-3-[(tert-butyl)dimethylsilyloxy]-1-{6-O-[(tert-butyl)diphenylsilyl]-3,4-O-isopropylidene-2-O-(3-methylbut-2-enyl)-β-D-galactopyranosyloxy}-12-[(1R,2S)-2-decylcyclopropyl]dec-7-ene

(2S,3R,7Z)-2-azido-3-[(tert-butyl)dimethylsilyloxy]-1-{6-O-[(tert-butyl)diphenylsilyl]-3,4-O-isopropylidene-β-D-galactopyranosyloxy}-12-[(1R,2S)-2-decylcyclopropyl]dodec-7-ene

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