(2R,3R,5R)-2-(tert-butyl-dimethyl-silanyloxy)-5,7,7-trimethoxy-3-(4'-methoxy-benzyloxy)-heptan-1-ol

Base Information

Chemical Name:(2R,3R,5R)-2-(tert-butyl-dimethyl-silanyloxy)-5,7,7-trimethoxy-3-(4'-methoxy-benzyloxy)-heptan-1-ol
CAS No.:213978-54-2
Molecular Formula:C₂₄H₄₄O₇Si
Molecular Weight:472.695
Hs Code.:

Synonyms:(2R,3R,5R)-2-(tert-butyl-dimethyl-silanyloxy)-5,7,7-trimethoxy-3-(4'-methoxy-benzyloxy)-heptan-1-ol

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Chemical Property of (2R,3R,5R)-2-(tert-butyl-dimethyl-silanyloxy)-5,7,7-trimethoxy-3-(4'-methoxy-benzyloxy)-heptan-1-ol

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Technology Process of (2R,3R,5R)-2-(tert-butyl-dimethyl-silanyloxy)-5,7,7-trimethoxy-3-(4'-methoxy-benzyloxy)-heptan-1-ol

There total 15 articles about (2R,3R,5R)-2-(tert-butyl-dimethyl-silanyloxy)-5,7,7-trimethoxy-3-(4'-methoxy-benzyloxy)-heptan-1-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: 89.0%

: 67-56-1
methanol

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

: 213978-54-2
(2R,3R,5R)-2-(tert-butyl-dimethyl-silanyloxy)-5,7,7-trimethoxy-3-(4'-methoxy-benzyloxy)-heptan-1-ol

Guidance literature:: With camphor-10-sulfonic acid;
DOI:10.1016/S0040-4039(98)01258-1

Reference yield:

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

: 213978-54-2
(2R,3R,5R)-2-(tert-butyl-dimethyl-silanyloxy)-5,7,7-trimethoxy-3-(4'-methoxy-benzyloxy)-heptan-1-ol

Guidance literature:: Multi-step reaction with 9 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

9.1: 89 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 1 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:

: 213978-52-0
(2R,3R,5S)-5-methoxy-3-(4'-methoxy-benzyloxy)-oct-7-ene-1,2-diol

: 213978-54-2
(2R,3R,5R)-2-(tert-butyl-dimethyl-silanyloxy)-5,7,7-trimethoxy-3-(4'-methoxy-benzyloxy)-heptan-1-ol

Guidance literature:: Multi-step reaction with 4 steps

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

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

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

4: 89 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 1 h / 20 °C

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