(R)-4-Benzyl-3-((R)-2-{(4S,5R,6S)-6-[(1S,2S,3R,5R,6S,7R,8R)-8-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-6-(4-methoxy-benzyloxy)-1,3,5,7-tetramethyl-4-oxo-decyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionyl)-oxazolidin-2-one

Base Information

• Chemical Name: (R)-4-Benzyl-3-((R)-2-{(4S,5R,6S)-6-[(1S,2S,3R,5R,6S,7R,8R)-8-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-6-(4-methoxy-benzyloxy)-1,3,5,7-tetramethyl-4-oxo-decyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionyl)-oxazolidin-2-one
• CAS No.: 171005-61-1
• Molecular Formula: C₄₈H₇₅NO₁₀Si
• Molecular Weight: 854.21

Synonyms:(R)-4-Benzyl-3-((R)-2-{(4S,5R,6S)-6-[(1S,2S,3R,5R,6S,7R,8R)-8-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-6-(4-methoxy-benzyloxy)-1,3,5,7-tetramethyl-4-oxo-decyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionyl)-oxazolidin-2-one

Chemical Property of (R)-4-Benzyl-3-((R)-2-{(4S,5R,6S)-6-[(1S,2S,3R,5R,6S,7R,8R)-8-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-6-(4-methoxy-benzyloxy)-1,3,5,7-tetramethyl-4-oxo-decyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionyl)-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (R)-4-Benzyl-3-((R)-2-{(4S,5R,6S)-6-[(1S,2S,3R,5R,6S,7R,8R)-8-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-6-(4-methoxy-benzyloxy)-1,3,5,7-tetramethyl-4-oxo-decyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionyl)-oxazolidin-2-one

There total 9 articles about (R)-4-Benzyl-3-((R)-2-{(4S,5R,6S)-6-[(1S,2S,3R,5R,6S,7R,8R)-8-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-6-(4-methoxy-benzyloxy)-1,3,5,7-tetramethyl-4-oxo-decyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionyl)-oxazolidin-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:

t-butyldimethylsiyl triflate (69739-34-0) → (R)-4-Benzyl-3-((R)-2-{(4S,5R,6S)-6-[(1S,2S,3R,5R,6S,7R,8R)-8-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-6-(4-methoxy-benzyloxy)-1,3,5,7-tetramethyl-4-oxo-decyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionyl)-oxazolidin-2-one (171005-61-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -5 °C

2: 1.) AlMe₃ / 1.) CH₂Cl₂, toluene, RT, 30 min, 2.) CH₂Cl₂, toluene, -14 deg C, 9 h

3: 86 percent / diethyl ether / a) 0 deg C, 3 h, b) RT, 2 h

4: 56 percent / triflic acid / diethyl ether / Ambient temperature

5: 1.) diphenyltetramethyldisilazine, n-BuLi, 2.) 2,6-lutidine / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, a) 0 deg C, 1 h, b) RT, 8 h

6: 83 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / -78 °C

With 2,6-dimethylpyridine; n-butyllithium; trifluorormethanesulfonic acid; diphenyltetramethyldisilazine; boron trifluoride diethyl etherate; trimethylaluminum; In diethyl ether; dichloromethane;

DOI:10.1021/ja9806128

Reference yield:

(R)-1-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2-methylpentane-1,3-dione (101712-01-0,141423-22-5,141423-21-4) → (R)-4-Benzyl-3-((R)-2-{(4S,5R,6S)-6-[(1S,2S,3R,5R,6S,7R,8R)-8-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-6-(4-methoxy-benzyloxy)-1,3,5,7-tetramethyl-4-oxo-decyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionyl)-oxazolidin-2-one (171005-61-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) Sn(OTf)2, Et₃N / 1.) CH₂Cl₂, -20 deg C, 1 h, 2.) CH₂Cl₂, -78 deg C, 1 h

2: 100 percent / NaBH₄, AcOH / 0.5 h / Ambient temperature

3: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -5 °C

4: 1.) AlMe₃ / 1.) CH₂Cl₂, toluene, RT, 30 min, 2.) CH₂Cl₂, toluene, -14 deg C, 9 h

5: 86 percent / diethyl ether / a) 0 deg C, 3 h, b) RT, 2 h

6: 56 percent / triflic acid / diethyl ether / Ambient temperature

7: 1.) diphenyltetramethyldisilazine, n-BuLi, 2.) 2,6-lutidine / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, a) 0 deg C, 1 h, b) RT, 8 h

8: 83 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / -78 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; tin(II) trifluoromethanesulfonate; n-butyllithium; trifluorormethanesulfonic acid; diphenyltetramethyldisilazine; boron trifluoride diethyl etherate; trimethylaluminum; acetic acid; triethylamine; In diethyl ether; dichloromethane;

DOI:10.1021/ja9806128

Reference yield:

(R)-4-Benzyl-3-[(2R,3S,4R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-heptanoyl]-oxazolidin-2-one (186489-73-6) → (R)-4-Benzyl-3-((R)-2-{(4S,5R,6S)-6-[(1S,2S,3R,5R,6S,7R,8R)-8-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-6-(4-methoxy-benzyloxy)-1,3,5,7-tetramethyl-4-oxo-decyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionyl)-oxazolidin-2-one (171005-61-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) AlMe₃ / 1.) CH₂Cl₂, toluene, RT, 30 min, 2.) CH₂Cl₂, toluene, -14 deg C, 9 h

2: 86 percent / diethyl ether / a) 0 deg C, 3 h, b) RT, 2 h

3: 56 percent / triflic acid / diethyl ether / Ambient temperature

4: 1.) diphenyltetramethyldisilazine, n-BuLi, 2.) 2,6-lutidine / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, a) 0 deg C, 1 h, b) RT, 8 h

5: 83 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / -78 °C

With 2,6-dimethylpyridine; n-butyllithium; trifluorormethanesulfonic acid; diphenyltetramethyldisilazine; boron trifluoride diethyl etherate; trimethylaluminum; In diethyl ether; dichloromethane;

DOI:10.1021/ja9806128

upstream raw materials:

t-butyldimethylsiyl triflate

(R)-1-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2-methylpentane-1,3-dione

(R)-4-Benzyl-3-[(2R,3S,4R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-heptanoyl]-oxazolidin-2-one

(4R,5S,6R,7R)-7-(t-butyldimethylsilyloxy)-5-hydroxy-4,6-dimethylnonan-3-one

Downstream raw materials:

(R)-4-Benzyl-3-((R)-2-{(4S,5R,6S)-6-[(1S,2R,3S,4S,5S,6R,7R,8R)-8-(tert-butyl-dimethyl-silanyloxy)-2,4-dihydroxy-6-(4-methoxy-benzyloxy)-1,3,5,7-tetramethyl-decyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionyl)-oxazolidin-2-one

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