(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

Base Information

Chemical Name:(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
CAS No.:208338-32-3
Molecular Formula:C₅₄H₇₀O₁₀S₂
Molecular Weight:943.276
Hs Code.:

(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

Synonyms:(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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Chemical Property of (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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Technology Process of (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

There total 18 articles about (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 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%

: 108-24-7
acetic anhydride

: 208338-30-1
(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

: 208338-32-3
(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

Guidance literature:: With dmap; In pyridine; at 80 ℃; for 30h;
DOI:10.1016/S0040-4039(98)00485-7

Reference yield:

: 171189-83-6
(2R,3R)-7-Benzyloxy-2-methyl-1-phenyl-heptan-3-ol

: 208338-32-3
(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

Guidance literature:: Multi-step reaction with 7 steps

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

2: 94 percent / BCl₃*SMe₂ / CH₂Cl₂ / 1 h / 20 °C

3: 97 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

4: 92 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / 20 °C

5: 65 percent / mCPBA / CH₂Cl₂ / 0.02 h / 0 °C

6: 230 mg

7: 85 percent / DMAP / pyridine / 3 h / 60 °C

With 1H-imidazole; dmap; oxalyl dichloride; boron trichloride - methyl sulfide complex; boron trifluoride diethyl etherate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In pyridine; dichloromethane; N,N-dimethyl-formamide; 1: Substitution / 2: Debenzylation / 3: Swern oxidation / 4: Thioacetal formation / 5: Oxidation / 7: Acetylation;
DOI:10.1021/jo000700m

Reference yield:

: 306281-48-1
(5R,6R)-5-(tert-butyldiphenylsilyloxy)-6-methyl-7-phenylheptan-1-ol

: 208338-32-3
(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

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

2: 92 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / 20 °C

3: 65 percent / mCPBA / CH₂Cl₂ / 0.02 h / 0 °C

4: 230 mg

5: 85 percent / DMAP / pyridine / 3 h / 60 °C

With dmap; oxalyl dichloride; boron trifluoride diethyl etherate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In pyridine; dichloromethane; 1: Swern oxidation / 2: Thioacetal formation / 3: Oxidation / 5: Acetylation;
DOI:10.1021/jo000700m