(3S,2'R,3'S,4'Z,6'R,7'S)-2-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}-1-(tert-butyldimethylsilyloxy)hex-5-en-3-ol

Base Information

Chemical Name:(3S,2'R,3'S,4'Z,6'R,7'S)-2-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}-1-(tert-butyldimethylsilyloxy)hex-5-en-3-ol
CAS No.:863222-67-7
Molecular Formula:C₃₆H₅₂O₆Si
Molecular Weight:608.891
Hs Code.:

Synonyms:(3S,2'R,3'S,4'Z,6'R,7'S)-2-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}-1-(tert-butyldimethylsilyloxy)hex-5-en-3-ol

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Chemical Property of (3S,2'R,3'S,4'Z,6'R,7'S)-2-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}-1-(tert-butyldimethylsilyloxy)hex-5-en-3-ol

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Technology Process of (3S,2'R,3'S,4'Z,6'R,7'S)-2-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}-1-(tert-butyldimethylsilyloxy)hex-5-en-3-ol

There total 14 articles about (3S,2'R,3'S,4'Z,6'R,7'S)-2-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}-1-(tert-butyldimethylsilyloxy)hex-5-en-3-ol 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: 88.0%

: 863222-46-2
(2R,3S,4Z,6R,7S,3'S,4'R)-2-allyl-6-benzyloxy-7-benzyloxymethyl-3-{1'-(tert-butyldimethylsilyloxy)-3',4'-epoxyhex-5'-en-2'-yl}oxy-2,3,6,7-tetrahydrooxepin

: 863222-67-7
(3S,2'R,3'S,4'Z,6'R,7'S)-2-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}-1-(tert-butyldimethylsilyloxy)hex-5-en-3-ol

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tri-n-butyl-tin hydride; In dichloromethane; at 24 ℃; for 0.416667h;
DOI:10.1016/j.tet.2005.05.073

Reference yield:

: 863222-50-8
(2R,3S,4Z,6R,7S)-2-allyl-6-benzyloxy-7-benzyloxymethyl-2,3,6,7-tetrahydrooxepin-3-ol

: 863222-67-7
(3S,2'R,3'S,4'Z,6'R,7'S)-2-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}-1-(tert-butyldimethylsilyloxy)hex-5-en-3-ol

Guidance literature:: Multi-step reaction with 11 steps

1.1: 98 percent / PMe₃ / tetrahydrofuran; CH₂Cl₂ / 0.5 h / 24 °C

2.1: 94 percent / DIBAH / CH₂Cl₂; hexane / 1 h / -78 °C

3.1: 84 percent / TPAP; NMO; 4 Angstroem molecular sieves / dimethylsulfoxide / 1.5 h / 23 °C

4.1: 74 percent / Me₃Al / benzene; hexane / 1 h / 25 °C

5.1: 63 percent / Bu₃SnH; BF₃*Et₂O / CH₂Cl₂ / 0.17 h / 0 °C

6.1: 83 percent / DIBAH / CH₂Cl₂; hexane / 1 h / -78 °C

7.1: 91 percent / DIBAH / CH₂Cl₂; hexane / 0.5 h / -78 °C

8.1: 76 percent / D-(-)-DET; Ti(O-iPr)4; TBHP / CH₂Cl₂ / 60 h / -25 °C

9.1: SO₃*pyridine; Et₃N; DMSO / CH₂Cl₂ / 3 h / 24 °C

10.1: NaHMDS / tetrahydrofuran / 1 h / 24 °C

10.2: 2.0 mg / CH₂Cl₂ / 60 h / 24 °C

11.1: 88 percent / Pd(PPh₃)4; Bu₃SnH / CH₂Cl₂ / 0.42 h / 24 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-methyl-2-indolinone; tetrapropylammonium perruthennate; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; 4 A molecular sieve; boron trifluoride diethyl etherate; trimethylaluminum; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; trimethylphosphane; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; benzene; 1.1: hetero-Michael addition / 8.1: Katsuki-Sharpless asymmetric epoxidation / 10.2: Wittig reaction;
DOI:10.1016/j.tet.2005.05.073

Reference yield:

: 863222-60-0
(2R,3S,4Z,6R,7S)-{6-benzyloxy-7-benzyloxymethyl-3-(4-methoxybenzyloxy)-2,3,6,7-tetrahydrooxepin-2-yl}ethanal

: 863222-67-7
(3S,2'R,3'S,4'Z,6'R,7'S)-2-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}-1-(tert-butyldimethylsilyloxy)hex-5-en-3-ol

Guidance literature:: Multi-step reaction with 13 steps

1.1: NaHMDS / tetrahydrofuran / 1 h / 20 °C

1.2: 100 percent / tetrahydrofuran / -78 - 22 °C

2.1: 92 percent / DDQ / CH₂Cl₂; H₂O / 3 h / 0 °C / pH 7

3.1: 98 percent / PMe₃ / tetrahydrofuran; CH₂Cl₂ / 0.5 h / 24 °C

4.1: 94 percent / DIBAH / CH₂Cl₂; hexane / 1 h / -78 °C

5.1: 84 percent / TPAP; NMO; 4 Angstroem molecular sieves / dimethylsulfoxide / 1.5 h / 23 °C

6.1: 74 percent / Me₃Al / benzene; hexane / 1 h / 25 °C

7.1: 63 percent / Bu₃SnH; BF₃*Et₂O / CH₂Cl₂ / 0.17 h / 0 °C

8.1: 83 percent / DIBAH / CH₂Cl₂; hexane / 1 h / -78 °C

9.1: 91 percent / DIBAH / CH₂Cl₂; hexane / 0.5 h / -78 °C

10.1: 76 percent / D-(-)-DET; Ti(O-iPr)4; TBHP / CH₂Cl₂ / 60 h / -25 °C

11.1: SO₃*pyridine; Et₃N; DMSO / CH₂Cl₂ / 3 h / 24 °C

12.1: NaHMDS / tetrahydrofuran / 1 h / 24 °C

12.2: 2.0 mg / CH₂Cl₂ / 60 h / 24 °C

13.1: 88 percent / Pd(PPh₃)4; Bu₃SnH / CH₂Cl₂ / 0.42 h / 24 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-methyl-2-indolinone; tetrapropylammonium perruthennate; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; 4 A molecular sieve; boron trifluoride diethyl etherate; trimethylaluminum; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; trimethylphosphane; In tetrahydrofuran; hexane; dichloromethane; water; dimethyl sulfoxide; benzene; 1.2: Wittig reaction / 3.1: hetero-Michael addition / 10.1: Katsuki-Sharpless asymmetric epoxidation / 12.2: Wittig reaction;
DOI:10.1016/j.tet.2005.05.073