(2R,3S,4S)-4-{(4R,6S)-6-[(1R,2S,4S)-6-Benzyloxy-2-methoxy-4-(4-methoxy-benzyloxy)-1-methyl-hexyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pentanal

Base Information

• Chemical Name: (2R,3S,4S)-4-{(4R,6S)-6-[(1R,2S,4S)-6-Benzyloxy-2-methoxy-4-(4-methoxy-benzyloxy)-1-methyl-hexyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pentanal
• CAS No.: 182571-79-5
• Molecular Formula: C₄₁H₆₆O₈Si
• Molecular Weight: 715.056
• Mol file: 182571-79-5.mol

Synonyms:(2R,3S,4S)-4-{(4R,6S)-6-[(1R,2S,4S)-6-Benzyloxy-2-methoxy-4-(4-methoxy-benzyloxy)-1-methyl-hexyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pentanal

Chemical Property of (2R,3S,4S)-4-{(4R,6S)-6-[(1R,2S,4S)-6-Benzyloxy-2-methoxy-4-(4-methoxy-benzyloxy)-1-methyl-hexyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pentanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S)-4-{(4R,6S)-6-[(1R,2S,4S)-6-Benzyloxy-2-methoxy-4-(4-methoxy-benzyloxy)-1-methyl-hexyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pentanal

There total 31 articles about (2R,3S,4S)-4-{(4R,6S)-6-[(1R,2S,4S)-6-Benzyloxy-2-methoxy-4-(4-methoxy-benzyloxy)-1-methyl-hexyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pentanal 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: 85.0%

(4S,5R,6S)-6-{(4R,6S)-6-[(1R,2S,4S)-6-Benzyloxy-2-methoxy-4-(4-methoxy-benzyloxy)-1-methyl-hexyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-5-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-4-methyl-heptanoic acid ethyl ester → (2R,3S,4S)-4-{(4R,6S)-6-[(1R,2S,4S)-6-Benzyloxy-2-methoxy-4-(4-methoxy-benzyloxy)-1-methyl-hexyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pentanal (182571-79-5)

Guidance literature:

With lead(IV) acetate; In toluene; Ambient temperature;

DOI:10.1016/0040-4039(96)01503-1

Reference yield:

p-methoxybenzyl chloride (824-94-2) → (2R,3S,4S)-4-{(4R,6S)-6-[(1R,2S,4S)-6-Benzyloxy-2-methoxy-4-(4-methoxy-benzyloxy)-1-methyl-hexyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pentanal (182571-79-5)

Guidance literature:

Multi-step reaction with 30 steps

1: 97 percent / NaH / dimethylformamide; tetrahydrofuran / Ambient temperature

2: MeI, NaHCO₃ / acetone; H₂O / 0 deg C to RT

3: toluene / 110 °C

4: 88 percent / DIBAH / toluene / -78 °C

5: t-BuOOH, L-(+)-DET, Ti(OiPr)4, 4A-MS / CH₂Cl₂ / -23 °C

6: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 deg C to RT

7: NaH / tetrahydrofuran / 0 deg C to RT

8: 96 percent / Pd₂(dba)3*CHCl₃, n-Bu₃P, HCOOH, Et₃N / dioxane / Ambient temperature

9: 100 percent / Ag₂O / acetonitrile / 85 °C

10: 83 percent / DIBAH / toluene / -78 °C

11: 87 percent / t-BuOOH, D-(-)-DET, Ti(OiPr)4, 4A-MS / CH₂Cl₂ / -23 °C

12: DMSO, (COCl)2, Et₃N / CH₂Cl₂ / -78 deg C to RT

13: toluene / 120 °C

14: 99 percent / Pd₂(dba)3*CHCl₃, nBu₃P, HCOOH, Et₃N / dioxane / Ambient temperature

15: 95 percent / imidazole / dimethylformamide / Ambient temperature

16: 80 percent / DIBAH / toluene / -78 °C

17: 78 percent / t-BuOOH, D-(-)-DET, Ti(OiPr)4, 4A-MS / CH₂Cl₂ / -23 °C

18: DMSO, (COCl)2, Et₃N / CH₂Cl₂ / -78 deg C to RT

19: n-BuLi / tetrahydrofuran / 0 °C

20: 72 percent / Pd₂(dba)3*CHCl₃, nBu₃P, HCOOH, Et₃N / dioxane / Ambient temperature

21: 75 percent / AcOH / H₂O / Ambient temperature

22: 88 percent / CSA / CH₂Cl₂ / Ambient temperature

23: 93 percent / DIBAH / toluene / -78 °C

24: 76 percent / t-BuOOH, L-(+)-DET, Ti(OiPr)4, 4A-MS / CH₂Cl₂ / -23 °C

25: DMSO, (COCl)2, Et₃N / CH₂Cl₂ / -78 deg C to RT

26: NaH / tetrahydrofuran / 0 deg C to RT

27: 78 percent / Pd₂(dba)3*CHCl₃, nBu₃P, HCOOH, Et₃N / dioxane / Ambient temperature

28: 82 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

29: 71 percent / OsO₄, NMO / acetone; H₂O; 2-methyl-propan-2-ol / Ambient temperature

30: 85 percent / Pb(OAc)4 / toluene / Ambient temperature

With 1H-imidazole; 2,6-dimethylpyridine; lead(IV) acetate; titanium(IV) isopropylate; tert.-butylhydroperoxide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; osmium(VIII) oxide; n-butyllithium; formic acid; N-methyl-2-indolinone; oxalyl dichloride; diethyl (2S,3S)-tartrate; diethyl (2R,3R)-tartrate; tributylphosphine; camphor-10-sulfonic acid; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; acetic acid; dimethyl sulfoxide; triethylamine; silver(l) oxide; methyl iodide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1016/0040-4039(96)01503-1

Reference yield:

(S)-4-Benzyloxy-1-[1,3]dithian-2-yl-butan-2-ol (173279-16-8) → (2R,3S,4S)-4-{(4R,6S)-6-[(1R,2S,4S)-6-Benzyloxy-2-methoxy-4-(4-methoxy-benzyloxy)-1-methyl-hexyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pentanal (182571-79-5)

Guidance literature:

Multi-step reaction with 30 steps

1: 97 percent / NaH / dimethylformamide; tetrahydrofuran / Ambient temperature

2: MeI, NaHCO₃ / acetone; H₂O / 0 deg C to RT

3: toluene / 110 °C

4: 88 percent / DIBAH / toluene / -78 °C

5: t-BuOOH, L-(+)-DET, Ti(OiPr)4, 4A-MS / CH₂Cl₂ / -23 °C

6: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 deg C to RT

7: NaH / tetrahydrofuran / 0 deg C to RT

8: 96 percent / Pd₂(dba)3*CHCl₃, n-Bu₃P, HCOOH, Et₃N / dioxane / Ambient temperature

9: 100 percent / Ag₂O / acetonitrile / 85 °C

10: 83 percent / DIBAH / toluene / -78 °C

11: 87 percent / t-BuOOH, D-(-)-DET, Ti(OiPr)4, 4A-MS / CH₂Cl₂ / -23 °C

12: DMSO, (COCl)2, Et₃N / CH₂Cl₂ / -78 deg C to RT

13: toluene / 120 °C

14: 99 percent / Pd₂(dba)3*CHCl₃, nBu₃P, HCOOH, Et₃N / dioxane / Ambient temperature

15: 95 percent / imidazole / dimethylformamide / Ambient temperature

16: 80 percent / DIBAH / toluene / -78 °C

17: 78 percent / t-BuOOH, D-(-)-DET, Ti(OiPr)4, 4A-MS / CH₂Cl₂ / -23 °C

18: DMSO, (COCl)2, Et₃N / CH₂Cl₂ / -78 deg C to RT

19: n-BuLi / tetrahydrofuran / 0 °C

20: 72 percent / Pd₂(dba)3*CHCl₃, nBu₃P, HCOOH, Et₃N / dioxane / Ambient temperature

21: 75 percent / AcOH / H₂O / Ambient temperature

22: 88 percent / CSA / CH₂Cl₂ / Ambient temperature

23: 93 percent / DIBAH / toluene / -78 °C

24: 76 percent / t-BuOOH, L-(+)-DET, Ti(OiPr)4, 4A-MS / CH₂Cl₂ / -23 °C

25: DMSO, (COCl)2, Et₃N / CH₂Cl₂ / -78 deg C to RT

26: NaH / tetrahydrofuran / 0 deg C to RT

27: 78 percent / Pd₂(dba)3*CHCl₃, nBu₃P, HCOOH, Et₃N / dioxane / Ambient temperature

28: 82 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

29: 71 percent / OsO₄, NMO / acetone; H₂O; 2-methyl-propan-2-ol / Ambient temperature

30: 85 percent / Pb(OAc)4 / toluene / Ambient temperature

With 1H-imidazole; 2,6-dimethylpyridine; lead(IV) acetate; titanium(IV) isopropylate; tert.-butylhydroperoxide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; osmium(VIII) oxide; n-butyllithium; formic acid; N-methyl-2-indolinone; oxalyl dichloride; diethyl (2S,3S)-tartrate; diethyl (2R,3R)-tartrate; tributylphosphine; camphor-10-sulfonic acid; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; acetic acid; dimethyl sulfoxide; triethylamine; silver(l) oxide; methyl iodide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1016/0040-4039(96)01503-1

upstream raw materials:

p-methoxybenzyl chloride

(S)-4-Benzyloxy-1-[1,3]dithian-2-yl-butan-2-ol

(E)-(R)-7-Benzyloxy-5-(4-methoxy-benzyloxy)-2-methyl-hept-2-en-1-ol

{(2S,3S)-3-[(S)-4-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-methyl-oxiranyl}-methanol

Downstream raw materials:

(3S,5S,6R)-5-Methoxy-3-(4-methoxy-benzyloxy)-6-[(4S,6R)-6-((S)-1-{(4S,5S,6S)-6-[(S)-3-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-1-methyl-propyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-heptan-1-ol

C₄₅H₇₄O₁₁

(R)-2-[(4S,5S,6S)-6-((S)-1-{(4R,6S)-6-[(1R,2S,4S)-6-Benzyloxy-2-methoxy-4-(4-methoxy-benzyloxy)-1-methyl-hexyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-4-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-butan-1-ol

C₅₀H₇₈O₁₂