(3R,4R,5R)-6-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hexan-2-one

Base Information

Chemical Name:(3R,4R,5R)-6-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hexan-2-one
CAS No.:676349-24-9
Molecular Formula:C₂₅H₄₆O₅Si₂
Molecular Weight:482.808
Hs Code.:

Synonyms:(3R,4R,5R)-6-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hexan-2-one

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Chemical Property of (3R,4R,5R)-6-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hexan-2-one

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Technology Process of (3R,4R,5R)-6-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hexan-2-one

There total 8 articles about (3R,4R,5R)-6-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hexan-2-one 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: 34.0%

: [2,3,5-tris-(tert-butyl-dimethyl-silanyloxy)-hex-4-enyloxymethyl]-benzene

: (4S,5R)-6-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-hexane-2,3-dione

: (3S,4R,5R)-6-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hexan-2-one

: 676349-24-9
(3R,4R,5R)-6-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hexan-2-one

Guidance literature:: With AD-mix-α; water; In tert-butyl alcohol; at 20 ℃; for 120h;
DOI:10.1055/s-2003-44979

Reference yield:

: 4039-82-1
Benzyl propargyl ether

: 676349-24-9
(3R,4R,5R)-6-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hexan-2-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: n-BuLi / tetrahydrofuran / -78 °C

1.2: 69 percent / tetrahydrofuran

2.1: 79 percent / REDAL / tetrahydrofuran / -20 °C

3.1: 79 percent / NBS; PPh₃ / tetrahydrofuran / -40 °C

4.1: 75 percent / DMPU / tetrahydrofuran / -78 °C

5.1: 78 percent / aq. AgNO₃; NCS / acetonitrile

6.1: 76 percent / KH / tetrahydrofuran

7.1: 62 percent / super AD-mix β; H2O / 2-methyl-propan-2-ol / 96 h / 0 °C

8.1: 94 percent / imidazole / dimethylformamide

9.1: 34 percent / super AD mix-α; H2O / 2-methyl-propan-2-ol / 120 h / 20 °C

With 1H-imidazole; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; AD-mix-β; AD-mix-α; N-chloro-succinimide; N-Bromosuccinimide; n-butyllithium; water; potassium hydride; silver nitrate; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
DOI:10.1055/s-2003-44979

Reference yield:

: 95409-25-9
4-(benzyloxy)but-2-ynal

: 676349-24-9
(3R,4R,5R)-6-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hexan-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: 79 percent / REDAL / tetrahydrofuran / -20 °C

2: 79 percent / NBS; PPh₃ / tetrahydrofuran / -40 °C

3: 75 percent / DMPU / tetrahydrofuran / -78 °C

4: 78 percent / aq. AgNO₃; NCS / acetonitrile

5: 76 percent / KH / tetrahydrofuran

6: 62 percent / super AD-mix β; H2O / 2-methyl-propan-2-ol / 96 h / 0 °C

7: 94 percent / imidazole / dimethylformamide

8: 34 percent / super AD mix-α; H2O / 2-methyl-propan-2-ol / 120 h / 20 °C

With 1H-imidazole; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; AD-mix-β; AD-mix-α; N-chloro-succinimide; N-Bromosuccinimide; water; potassium hydride; silver nitrate; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
DOI:10.1055/s-2003-44979