(3R,4S,5R,6R,8R,10R,11R,12S,13R,14S)-3,4-bis<(benzyloxy)methoxy>-5,13-dihydroxy-10,11-(isopropylidenedioxy)-4,6,8,10,12,14-hexamethylhexadec-15-en-7-one

Base Information

Chemical Name:(3R,4S,5R,6R,8R,10R,11R,12S,13R,14S)-3,4-bis<(benzyloxy)methoxy>-5,13-dihydroxy-10,11-(isopropylidenedioxy)-4,6,8,10,12,14-hexamethylhexadec-15-en-7-one
CAS No.:159170-71-5
Molecular Formula:C₄₁H₆₂O₉
Molecular Weight:698.938
Hs Code.:

(3R,4S,5R,6R,8R,10R,11R,12S,13R,14S)-3,4-bis<(benzyloxy)methoxy>-5,13-dihydroxy-10,11-(isopropylidenedioxy)-4,6,8,10,12,14-hexamethylhexadec-15-en-7-one

Synonyms:(3R,4S,5R,6R,8R,10R,11R,12S,13R,14S)-3,4-bis<(benzyloxy)methoxy>-5,13-dihydroxy-10,11-(isopropylidenedioxy)-4,6,8,10,12,14-hexamethylhexadec-15-en-7-one

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Chemical Property of (3R,4S,5R,6R,8R,10R,11R,12S,13R,14S)-3,4-bis<(benzyloxy)methoxy>-5,13-dihydroxy-10,11-(isopropylidenedioxy)-4,6,8,10,12,14-hexamethylhexadec-15-en-7-one

Chemical Property:

Purity/Quality:

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Technology Process of (3R,4S,5R,6R,8R,10R,11R,12S,13R,14S)-3,4-bis<(benzyloxy)methoxy>-5,13-dihydroxy-10,11-(isopropylidenedioxy)-4,6,8,10,12,14-hexamethylhexadec-15-en-7-one

There total 17 articles about (3R,4S,5R,6R,8R,10R,11R,12S,13R,14S)-3,4-bis<(benzyloxy)methoxy>-5,13-dihydroxy-10,11-(isopropylidenedioxy)-4,6,8,10,12,14-hexamethylhexadec-15-en-7-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:

: 3587-60-8
Benzyloxymethyl chloride

: 159170-71-5
(3R,4S,5R,6R,8R,10R,11R,12S,13R,14S)-3,4-bis<(benzyloxy)methoxy>-5,13-dihydroxy-10,11-(isopropylidenedioxy)-4,6,8,10,12,14-hexamethylhexadec-15-en-7-one

Guidance literature:: Multi-step reaction with 4 steps

1: 84 percent / NaI, Proton Sponge / 1,2-dimethoxy-ethane / 40 h / Ambient temperature

2: 87 percent / MeLi / diethyl ether / 0.5 h / 0 °C

3: 1.) (SOCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 15 min, 2.) CH₂Cl₂, from -60 deg C to RT, 1.1 h

4: 1.) lithium hexamethyldisilazide / 1.) THF, -78 deg C, 2.5 h, 2.) THF, -78 deg C, 30 min

With thionyl chloride; Proton Sponge; methyllithium; dimethyl sulfoxide; triethylamine; sodium iodide; lithium hexamethyldisilazane; In 1,2-dimethoxyethane; diethyl ether;
DOI:10.1021/ja00090a016

Reference yield:

: 96481-55-9,2088-07-5
2-methylpent-1-en-3-ol

: 159170-71-5
(3R,4S,5R,6R,8R,10R,11R,12S,13R,14S)-3,4-bis<(benzyloxy)methoxy>-5,13-dihydroxy-10,11-(isopropylidenedioxy)-4,6,8,10,12,14-hexamethylhexadec-15-en-7-one

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) Ti(O-i-Pr)4, t-BuOOH, 4A-molecular sieves, diisopropyl D-tartarate / 1.) CH₂Cl₂, 2,2,4-trimethylpentane, -20 deg C, 30 min, 2.) CH₂Cl₂, 2,2,4-trimethylpentane, -20 deg C, 11 h

2: 63 percent / Ti(O-i-Pr)4 / CH₂Cl₂ / 40 h / Ambient temperature

3: 84 percent / NaI, Proton Sponge / 1,2-dimethoxy-ethane / 40 h / Ambient temperature

4: 87 percent / MeLi / diethyl ether / 0.5 h / 0 °C

5: 1.) (SOCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 15 min, 2.) CH₂Cl₂, from -60 deg C to RT, 1.1 h

6: 1.) lithium hexamethyldisilazide / 1.) THF, -78 deg C, 2.5 h, 2.) THF, -78 deg C, 30 min

With titanium(IV) isopropylate; tert.-butylhydroperoxide; thionyl chloride; Proton Sponge; 4 A molecular sieve; methyllithium; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; sodium iodide; lithium hexamethyldisilazane; In 1,2-dimethoxyethane; diethyl ether; dichloromethane;
DOI:10.1021/ja00090a016

Reference yield:

: 23074-10-4
5-ethylfurfural

: 159170-71-5
(3R,4S,5R,6R,8R,10R,11R,12S,13R,14S)-3,4-bis<(benzyloxy)methoxy>-5,13-dihydroxy-10,11-(isopropylidenedioxy)-4,6,8,10,12,14-hexamethylhexadec-15-en-7-one

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) di-n-butylboron triflate, Et₃N, 3.) 30percent aq. H₂O₂

2: 94 percent / LiBH₄ / tetrahydrofuran / 1.) -45 deg C, 1 h, 2.) 0 deg C, 2 h

3: 69 percent / Br₂ / H₂O; acetonitrile / 1.) -20 deg C, 30 min, 2.) RT, 30 min

4: 90 percent / CuI / diethyl ether / 1.25 h / -78 - -10 °C

5: 1.) cerium(III) chloride / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 1.5 h

6: 771 mg / TiCl₄ / CH₂Cl₂ / 1.) -78 deg C, 1 h, 2.) RT, 1.5 h

7: camphorsulfonic acid / 2 h / Ambient temperature

8: 89 percent / aq. bis(trifluoroacetoxy)iodobenzene / methanol / 0.17 h / 0 °C

9: 1.) (SOCl)2, DMSO, 2.) pyridine / 1.) CH₂Cl₂, -60 deg C, 15 min, 2.) CH₂Cl₂, from -60 deg C to RT, 45 min

10: 1.) BF₃*Et₂O / 1.) CH₂Cl₂, -90 deg C, 5 min, 2.) CH₂Cl₂, -90 deg C 30 min

11: 1.) lithium hexamethyldisilazide / 1.) THF, -78 deg C, 2.5 h, 2.) THF, -78 deg C, 30 min

With pyridine; copper(l) iodide; lithium borohydride; thionyl chloride; cerium(III) chloride; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; dihydrogen peroxide; bromine; titanium tetrachloride; dimethyl sulfoxide; triethylamine; bis-[(trifluoroacetoxy)iodo]benzene; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetonitrile;
DOI:10.1021/ja00090a016