(3R,5R,6R)-6,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-5-(4'-methoxy-benzyloxy)-heptanal

Base Information

Chemical Name:(3R,5R,6R)-6,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-5-(4'-methoxy-benzyloxy)-heptanal
CAS No.:213978-53-1
Molecular Formula:C₂₈H₅₂O₆Si₂
Molecular Weight:540.888
Hs Code.:

Synonyms:(3R,5R,6R)-6,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-5-(4'-methoxy-benzyloxy)-heptanal

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Chemical Property of (3R,5R,6R)-6,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-5-(4'-methoxy-benzyloxy)-heptanal

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Technology Process of (3R,5R,6R)-6,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-5-(4'-methoxy-benzyloxy)-heptanal

There total 15 articles about (3R,5R,6R)-6,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-5-(4'-methoxy-benzyloxy)-heptanal 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: 94.0%

: 213978-67-7
(4S,6R,7R)-7,8-bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-6-(4'-methoxy-benzyloxy)-oct-1-ene

: 213978-53-1
(3R,5R,6R)-6,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-5-(4'-methoxy-benzyloxy)-heptanal

Guidance literature:: With sodium periodate; osmium(VIII) oxide;
DOI:10.1016/S0040-4039(98)01258-1

Reference yield:

: 67320-20-1
2-deoxy-4,5-O-isopropylidene-D-threo-pentose diethyl dithioacetal

: 213978-53-1
(3R,5R,6R)-6,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-5-(4'-methoxy-benzyloxy)-heptanal

Guidance literature:: Multi-step reaction with 8 steps

1.1: t-BuOK / tetrahydrofuran / 1 h / -20 °C

1.2: 98 percent / NBu₄I / tetrahydrofuran / 15 h / 20 °C

2.1: 91 percent / aq. CaCO₃; Hg(ClO₄)2 / tetrahydrofuran / 3 h / 20 °C

3.1: diethyl ether / 3 h / -78 °C

3.2: 4.69 g / aq. NaOH; H₂O₂ / diethyl ether / 2 h / Heating

4.1: t-BuOK / tetrahydrofuran / 0.5 h / -20 °C

4.2: 97 percent / tetrahydrofuran / 6 h / 20 °C

5.1: 88 percent / 10-camphorsulfonic acid / methanol / 6 h / 0 - 20 °C

6.1: 98 percent / Et₃N / CH₂Cl₂ / 1 h / 0 - 20 °C

7.1: NMO; aq. OsO₄ / acetone / 12 h / 20 °C

8.1: 6.2 g / aq. NaIO₄; silica / petroleum ether; CH₂Cl₂ / 3 h / 20 °C

With sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; mercury(II) perchlorate; (1S)-10-camphorsulfonic acid; potassium tert-butylate; silica gel; triethylamine; calcium carbonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; Petroleum ether;
DOI:10.1039/b308305e

Reference yield:

: 213978-50-8
(3R,4'R)-3-(2,2'-dimethyl-[1',3']-dioxolan-4'-yl)-3-(4''-methoxy-benzyloxy)-propionaldehyde

: 213978-53-1
(3R,5R,6R)-6,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-5-(4'-methoxy-benzyloxy)-heptanal

Guidance literature:: Multi-step reaction with 6 steps

1.1: diethyl ether / 3 h / -78 °C

1.2: 4.69 g / aq. NaOH; H₂O₂ / diethyl ether / 2 h / Heating

2.1: t-BuOK / tetrahydrofuran / 0.5 h / -20 °C

2.2: 97 percent / tetrahydrofuran / 6 h / 20 °C

3.1: 88 percent / 10-camphorsulfonic acid / methanol / 6 h / 0 - 20 °C

4.1: 98 percent / Et₃N / CH₂Cl₂ / 1 h / 0 - 20 °C

5.1: NMO; aq. OsO₄ / acetone / 12 h / 20 °C

6.1: 6.2 g / aq. NaIO₄; silica / petroleum ether; CH₂Cl₂ / 3 h / 20 °C

With sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; (1S)-10-camphorsulfonic acid; potassium tert-butylate; silica gel; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; Petroleum ether;
DOI:10.1039/b308305e