{2-[(4R,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-6-phenyl-hexyl]-1-oxo-1λ⁴-[1,3]dithian-2-yl}-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methanol

Base Information

• Chemical Name: {2-[(4R,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-6-phenyl-hexyl]-1-oxo-1λ⁴-[1,3]dithian-2-yl}-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methanol
• CAS No.: 306306-46-7
• Molecular Formula: C₆₈H₈₆O₁₀S₂Si
• Molecular Weight: 1155.64

Synonyms:

Chemical Property of {2-[(4R,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-6-phenyl-hexyl]-1-oxo-1λ⁴-[1,3]dithian-2-yl}-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of {2-[(4R,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-6-phenyl-hexyl]-1-oxo-1λ⁴-[1,3]dithian-2-yl}-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methanol

There total 7 articles about {2-[(4R,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-6-phenyl-hexyl]-1-oxo-1λ⁴-[1,3]dithian-2-yl}-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methanol 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:

tert-Butyl-[(R)-1-((R)-1-methyl-2-phenyl-ethyl)-4-(1-oxo-1λ4-[1,3]dithian-2-yl)-butoxy]-diphenyl-silane (208338-27-6) + (2S,3R,4S,5R)-2,3,4,5-bis(di-O-isopropylidene)-6-benzyloxy-(3,4-bis(benzyloxymethyl))hexan-1-al (172790-40-8) → {2-[(4R,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-6-phenyl-hexyl]-1-oxo-1λ4-[1,3]dithian-2-yl}-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methanol (306306-46-7)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1016/S0040-4039(98)00485-7

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → {2-[(4R,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-6-phenyl-hexyl]-1-oxo-1λ4-[1,3]dithian-2-yl}-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methanol (306306-46-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / imidazole / dimethylformamide / 24 h / 100 °C

2: 93 percent / BCl₃*Me₂S / CH₂Cl₂ / 1 h / Ambient temperature

3: 97 percent / 1.) (COCl)2/DMSO; 2.) Et₃N / 1.) CH₂Cl₂

4: 92 percent / BF₃*OEt₂ / CH₂Cl₂ / 1 h / Ambient temperature

5: 78 percent / mCPBA / CH₂Cl₂ / 0 °C

6: BuLi / tetrahydrofuran / 0.5 h / -78 °C

With 1H-imidazole; n-butyllithium; oxalyl dichloride; boron trichloride - methyl sulfide complex; boron trifluoride diethyl etherate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(98)00485-7

Reference yield:

(2R,3R)-7-Benzyloxy-2-methyl-1-phenyl-heptan-3-ol (171189-83-6) → {2-[(4R,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-6-phenyl-hexyl]-1-oxo-1λ4-[1,3]dithian-2-yl}-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methanol (306306-46-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / imidazole / dimethylformamide / 24 h / 100 °C

2: 93 percent / BCl₃*Me₂S / CH₂Cl₂ / 1 h / Ambient temperature

3: 97 percent / 1.) (COCl)2/DMSO; 2.) Et₃N / 1.) CH₂Cl₂

4: 92 percent / BF₃*OEt₂ / CH₂Cl₂ / 1 h / Ambient temperature

5: 78 percent / mCPBA / CH₂Cl₂ / 0 °C

6: BuLi / tetrahydrofuran / 0.5 h / -78 °C

With 1H-imidazole; n-butyllithium; oxalyl dichloride; boron trichloride - methyl sulfide complex; boron trifluoride diethyl etherate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(98)00485-7

upstream raw materials:

tert-Butyl-[(R)-1-((R)-1-methyl-2-phenyl-ethyl)-4-(1-oxo-1λ⁴-[1,3]dithian-2-yl)-butoxy]-diphenyl-silane

(2S,3R,4S,5R)-2,3,4,5-bis(di-O-isopropylidene)-6-benzyloxy-(3,4-bis(benzyloxymethyl))hexan-1-al

tert-butylchlorodiphenylsilane

(2R,3R)-7-Benzyloxy-2-methyl-1-phenyl-heptan-3-ol

Downstream raw materials:

(4'R,5'R,1''R,2''R,3''R,4''S,5''R)-2-[6''-benzyloxy-3'',4''-bis(benzyloxymethyl)-2'',3'',4'',5''-bis(di-O-isopropylidene)-1''-hydroxyhex-1''-yl]-2-[4'-hydroxy-5'-methyl-6'-phenylhex-1'-yl][1,3]dithiane

(4'R,5'R,1''S,2''R,3''R,4''S,5''S)-2-[6''-benzyloxy-3'',4''-bis(benzyloxymethyl)-2'',3'',4'',5''-bis(di-O-isopropylidene)-1''-hydroxyhex-1''-yl]-2-[4'-hydroxy-5'-methyl-6'-phenylhex-1'-yl][1,3]dithiane

(4'R,5'R,1''R,2''R,3''R,4''S,5''R)-2-[4'-acetoxy-5'-methyl-6'-phenyl-hex-1'-yl]-2-[6''-benzyloxy-3'',4''-bis(benzyloxymethyl)-2'',3'',4'',5''-bis(di-O-isopropylidene)-1''-hydroxyhex-1''-yl][1,3]dithiane

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