(1S,2R,3R,5R)-5-benzyloxy-3-<(1R,2S)-3-(tert-butyldimethylsilyloxy)-1,2-dihydroxypropyl>-1-(methoxymethoxy)-2-(triethylsilyloxy)cyclohexane

Base Information

Chemical Name:(1S,2R,3R,5R)-5-benzyloxy-3-<(1R,2S)-3-(tert-butyldimethylsilyloxy)-1,2-dihydroxypropyl>-1-(methoxymethoxy)-2-(triethylsilyloxy)cyclohexane
CAS No.:141318-33-4
Molecular Formula:C₃₀H₅₆O₇Si₂
Molecular Weight:584.941
Hs Code.:

Synonyms:(1S,2R,3R,5R)-5-benzyloxy-3-<(1R,2S)-3-(tert-butyldimethylsilyloxy)-1,2-dihydroxypropyl>-1-(methoxymethoxy)-2-(triethylsilyloxy)cyclohexane

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Chemical Property of (1S,2R,3R,5R)-5-benzyloxy-3-<(1R,2S)-3-(tert-butyldimethylsilyloxy)-1,2-dihydroxypropyl>-1-(methoxymethoxy)-2-(triethylsilyloxy)cyclohexane

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Technology Process of (1S,2R,3R,5R)-5-benzyloxy-3-<(1R,2S)-3-(tert-butyldimethylsilyloxy)-1,2-dihydroxypropyl>-1-(methoxymethoxy)-2-(triethylsilyloxy)cyclohexane

There total 14 articles about (1S,2R,3R,5R)-5-benzyloxy-3-<(1R,2S)-3-(tert-butyldimethylsilyloxy)-1,2-dihydroxypropyl>-1-(methoxymethoxy)-2-(triethylsilyloxy)cyclohexane 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: 44.0%

: 141276-79-1
(1S,2R,3S,5R)-5-benzyloxy-3-<(Z)-3-(tert-butyldimethylsilyloxy)prop-1-enyl>-1-methoxymethoxy-2-(triethylsilyloxy)cyclohexane

: 141318-33-4
(1S,2R,3R,5R)-5-benzyloxy-3-<(1R,2S)-3-(tert-butyldimethylsilyloxy)-1,2-dihydroxypropyl>-1-(methoxymethoxy)-2-(triethylsilyloxy)cyclohexane

: 141276-80-4
(1S,2R,3R,5R)-5-benzyloxy-3-<(1S,2R)-3-(tert-butyldimethylsilyloxy)-1,2-dihydroxypropyl>-1-(methoxymethoxy)-2-(triethylsilyloxy)cyclohexane

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; Ambient temperature;
DOI:10.1039/c39920000406

Reference yield:

: 994-30-9
triethylsilyl chloride

: 141318-33-4
(1S,2R,3R,5R)-5-benzyloxy-3-<(1R,2S)-3-(tert-butyldimethylsilyloxy)-1,2-dihydroxypropyl>-1-(methoxymethoxy)-2-(triethylsilyloxy)cyclohexane

Guidance literature:: Multi-step reaction with 7 steps

1: 97 percent / pyridine / 60 °C

2: 87 percent / MeONa / methanol / Ambient temperature

3: pyridinium chlorochromate (PCC) / CH₂Cl₂

4: 68 percent / potassium hexamethyldisilazane, 18-crown-6 / tetrahydrofuran / -78 °C

5: (i-Bu)2AlH / CH₂Cl₂ / -78 °C

6: 97 percent / 4-(N,N-dimethylamino)pyridine, Et₃N / CH₂Cl₂ / Ambient temperature

7: 48 percent / OsO₄, N-methylmorpholine N-oxide (NMO) / acetone; H₂O / Ambient temperature

With pyridine; dmap; osmium(VIII) oxide; potassium hexamethyldisilazane; 18-crown-6 ether; sodium methylate; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; water; acetone;
DOI:10.1039/c39920000406

Reference yield:

: 100-39-0
benzyl bromide

: 141318-33-4
(1S,2R,3R,5R)-5-benzyloxy-3-<(1R,2S)-3-(tert-butyldimethylsilyloxy)-1,2-dihydroxypropyl>-1-(methoxymethoxy)-2-(triethylsilyloxy)cyclohexane

Guidance literature:: Multi-step reaction with 10 steps

1: NaH / dimethylformamide / Ambient temperature

2: AcOH, H₂O / Ambient temperature

3: pyridine

4: 97 percent / pyridine / 60 °C

5: 87 percent / MeONa / methanol / Ambient temperature

6: pyridinium chlorochromate (PCC) / CH₂Cl₂

7: 68 percent / potassium hexamethyldisilazane, 18-crown-6 / tetrahydrofuran / -78 °C

8: (i-Bu)2AlH / CH₂Cl₂ / -78 °C

9: 97 percent / 4-(N,N-dimethylamino)pyridine, Et₃N / CH₂Cl₂ / Ambient temperature

10: 48 percent / OsO₄, N-methylmorpholine N-oxide (NMO) / acetone; H₂O / Ambient temperature

With pyridine; dmap; osmium(VIII) oxide; potassium hexamethyldisilazane; 18-crown-6 ether; water; sodium methylate; sodium hydride; diisobutylaluminium hydride; acetic acid; 4-methylmorpholine N-oxide; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1039/c39920000406