(3R)-4-[(2R,4R,6R)-4-p-methoxybenzyloxy-2-methoxy-2-methyltetrahydropyran-6-yl]-3-methoxy-1-tert-butyldiphenylsiloxy-2-butylazide

Base Information

Chemical Name:(3R)-4-[(2R,4R,6R)-4-p-methoxybenzyloxy-2-methoxy-2-methyltetrahydropyran-6-yl]-3-methoxy-1-tert-butyldiphenylsiloxy-2-butylazide
CAS No.:322428-59-1
Molecular Formula:C₃₆H₄₉N₃O₆Si
Molecular Weight:647.887
Hs Code.:

Synonyms:(3R)-4-[(2R,4R,6R)-4-p-methoxybenzyloxy-2-methoxy-2-methyltetrahydropyran-6-yl]-3-methoxy-1-tert-butyldiphenylsiloxy-2-butylazide

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Chemical Property of (3R)-4-[(2R,4R,6R)-4-p-methoxybenzyloxy-2-methoxy-2-methyltetrahydropyran-6-yl]-3-methoxy-1-tert-butyldiphenylsiloxy-2-butylazide

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Technology Process of (3R)-4-[(2R,4R,6R)-4-p-methoxybenzyloxy-2-methoxy-2-methyltetrahydropyran-6-yl]-3-methoxy-1-tert-butyldiphenylsiloxy-2-butylazide

There total 9 articles about (3R)-4-[(2R,4R,6R)-4-p-methoxybenzyloxy-2-methoxy-2-methyltetrahydropyran-6-yl]-3-methoxy-1-tert-butyldiphenylsiloxy-2-butylazide 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:

: 322429-00-5
Methanesulfonic acid (R)-1-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-3-[(2R,4R,6R)-6-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-yl]-propyl ester

: 322428-59-1
(3R)-4-[(2R,4R,6R)-4-p-methoxybenzyloxy-2-methoxy-2-methyltetrahydropyran-6-yl]-3-methoxy-1-tert-butyldiphenylsiloxy-2-butylazide

Guidance literature:: With tetrabutylammoniun azide; In tetrahydrofuran; N,N-dimethyl-formamide; at 100 ℃; for 4h;
DOI:10.1016/S0040-4020(01)00593-2

Reference yield:

: 322428-47-7
(4S)-5-[(4R,6R)-4-((E)-2-phenylethenyl)-2,2-dimethyl-1,3-dioxan-6-yl]-4-p-methoxybenzyloxy-2-pentene

: 322428-59-1
(3R)-4-[(2R,4R,6R)-4-p-methoxybenzyloxy-2-methoxy-2-methyltetrahydropyran-6-yl]-3-methoxy-1-tert-butyldiphenylsiloxy-2-butylazide

Guidance literature:: Multi-step reaction with 10 steps

1.1: 77 percent / O₂; PdCl₂; Cu(OAc)2*H₂O / N,N-dimethyl-acetamide; H₂O / 19.5 h / 20 °C

2.1: 85 percent / PPTS / methanol / 6.5 h

3.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

3.2: 98 percent / tetrahydrofuran / 14.67 h / 0 - 20 °C

4.1: OsO₄; NMO / acetone; H₂O; 2-methyl-propan-2-ol / 5 h / 20 °C

5.1: NaIO₄; sodium phosphate / tetrahydrofuran; H₂O / 0.42 h / 0 - 20 °C / pH 7

6.1: 134 mg / tetrahydrofuran; toluene / 0.2 h / -78 - 0 °C

7.1: 83 mg / OsO₄; NMO / acetone; H₂O; 2-methyl-propan-2-ol / 4.5 h / 20 °C

8.1: 129 mg / Et₃N; DMAP / CH₂Cl₂ / 13.83 h / 0 - 20 °C

9.1: Et₃N; DMAP / CH₂Cl₂ / 2.25 h / 0 - 20 °C

10.1: 75 mg / n-Bu₄NN₃ / dimethylformamide; tetrahydrofuran / 4 h / 100 °C

With dmap; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; copper diacetate; oxygen; tetrabutylammoniun azide; pyridinium p-toluenesulfonate; sodium hydride; triethylamine; sodium phosphate; palladium dichloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; 1.1: Wacker oxidation / 6.1: Tebbe olefination;
DOI:10.1016/S0040-4020(01)00593-2

Reference yield:

: 322428-51-3
(1E,3R)-4-[(2R,4R,6R)-4-p-methoxybenzyloxy-2-methoxy-2-methyltetrahydropyran-6-yl]-1-phenyl-3-hydroxy-1-butene

: 322428-59-1
(3R)-4-[(2R,4R,6R)-4-p-methoxybenzyloxy-2-methoxy-2-methyltetrahydropyran-6-yl]-3-methoxy-1-tert-butyldiphenylsiloxy-2-butylazide

Guidance literature:: Multi-step reaction with 8 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

1.2: 98 percent / tetrahydrofuran / 14.67 h / 0 - 20 °C

2.1: OsO₄; NMO / acetone; H₂O; 2-methyl-propan-2-ol / 5 h / 20 °C

3.1: NaIO₄; sodium phosphate / tetrahydrofuran; H₂O / 0.42 h / 0 - 20 °C / pH 7

4.1: 134 mg / tetrahydrofuran; toluene / 0.2 h / -78 - 0 °C

5.1: 83 mg / OsO₄; NMO / acetone; H₂O; 2-methyl-propan-2-ol / 4.5 h / 20 °C

6.1: 129 mg / Et₃N; DMAP / CH₂Cl₂ / 13.83 h / 0 - 20 °C

7.1: Et₃N; DMAP / CH₂Cl₂ / 2.25 h / 0 - 20 °C

8.1: 75 mg / n-Bu₄NN₃ / dimethylformamide; tetrahydrofuran / 4 h / 100 °C

With dmap; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; tetrabutylammoniun azide; sodium hydride; triethylamine; sodium phosphate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; 4.1: Tebbe olefination;
DOI:10.1016/S0040-4020(01)00593-2