(2S,6S,7S,9S,15R)-15-{(2S,5R,6R,8S)-5-Benzyloxy-8-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-15-methyl-2,9-diphenyl-1,8,13,16-tetraoxa-dispiro[5.0.5.4]hexadecan-14-one

Base Information

Chemical Name:(2S,6S,7S,9S,15R)-15-{(2S,5R,6R,8S)-5-Benzyloxy-8-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-15-methyl-2,9-diphenyl-1,8,13,16-tetraoxa-dispiro[5.0.5.4]hexadecan-14-one
CAS No.:220691-14-5
Molecular Formula:C₆₂H₇₄O₉Si
Molecular Weight:991.35
Hs Code.:

(2S,6S,7S,9S,15R)-15-{(2S,5R,6R,8S)-5-Benzyloxy-8-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-15-methyl-2,9-diphenyl-1,8,13,16-tetraoxa-dispiro[5.0.5.4]hexadecan-14-one

Synonyms:(2S,6S,7S,9S,15R)-15-{(2S,5R,6R,8S)-5-Benzyloxy-8-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-15-methyl-2,9-diphenyl-1,8,13,16-tetraoxa-dispiro[5.0.5.4]hexadecan-14-one

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Chemical Property of (2S,6S,7S,9S,15R)-15-{(2S,5R,6R,8S)-5-Benzyloxy-8-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-15-methyl-2,9-diphenyl-1,8,13,16-tetraoxa-dispiro[5.0.5.4]hexadecan-14-one

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Technology Process of (2S,6S,7S,9S,15R)-15-{(2S,5R,6R,8S)-5-Benzyloxy-8-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-15-methyl-2,9-diphenyl-1,8,13,16-tetraoxa-dispiro[5.0.5.4]hexadecan-14-one

There total 15 articles about (2S,6S,7S,9S,15R)-15-{(2S,5R,6R,8S)-5-Benzyloxy-8-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-15-methyl-2,9-diphenyl-1,8,13,16-tetraoxa-dispiro[5.0.5.4]hexadecan-14-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: 92.0%

: 100-39-0
benzyl bromide

: 220691-67-8
(2S,6S,7S,9S,15R)-15-{(2S,5R,6R,8S)-8-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-5-hydroxy-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-15-methyl-2,9-diphenyl-1,8,13,16-tetraoxa-dispiro[5.0.5.4]hexadecan-14-one

: 220691-14-5
(2S,6S,7S,9S,15R)-15-{(2S,5R,6R,8S)-5-Benzyloxy-8-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-15-methyl-2,9-diphenyl-1,8,13,16-tetraoxa-dispiro[5.0.5.4]hexadecan-14-one

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride;

Reference yield:

: 154859-09-3
(6S,6'S)-6,6'-Diphenyl-5,6,5',6'-tetrahydro-4H,4'H-[2,2']bipyranyl

: 220691-14-5
(2S,6S,7S,9S,15R)-15-{(2S,5R,6R,8S)-5-Benzyloxy-8-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-15-methyl-2,9-diphenyl-1,8,13,16-tetraoxa-dispiro[5.0.5.4]hexadecan-14-one

Guidance literature:: Multi-step reaction with 12 steps

1: 89 percent / Ph₃P*HBr / CH₂Cl₂

2: 1.) LDA, DMPU, 2.) BuLi / 1.) THF, PhMe, -78 deg C, 2.) THF, PhMe

3: 1.) LDA, DMPU, 2.) BuLi / 1.) THF, DME, -78 deg C, 2.) THF, DME, -78 deg C to r.t.

4: 82 percent / K₂OsO₂(OH)4, (DHQD)2PYR, K₃Fe(CN)6, H₂O / 2-methyl-propan-2-ol / 0 °C

6: 1.) BuLi, CuCN, LiCl, 2.) BF₃*Et₂O / 1.) THF, -78 deg C, 2.) THF

7: 1.) BH₃*SMe₂, 2.) H₂O₂, phosphate buffer (pH 7) / 1.) THF, 2.) THF

8: 78 percent / TPAP, NMO, molecular sieves 4 Angstroem / CH₂Cl₂ / 0 °C

10: 79 percent / H₂O, AcOH / tetrahydrofuran

11: 90 percent / NaBH₄ / ethanol / 0 °C

12: 92 percent / NaH, Bu₄NI

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium tetrahydroborate; n-butyllithium; N-methyl-2-indolinone; phosphate buffer; tetrapropylammonium perruthennate; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; potassium dioxotetrahydroxoosmate(VI); dimethylsulfide borane complex; 4 A molecular sieve; boron trifluoride diethyl etherate; water; dihydrogen peroxide; triphenylphosphine hydrobromide; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; lithium chloride; potassium hexacyanoferrate(III); lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane; tert-butyl alcohol;

Reference yield:

: (S)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,3-dihydro-pyran-4-one

: 220691-14-5
(2S,6S,7S,9S,15R)-15-{(2S,5R,6R,8S)-5-Benzyloxy-8-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-15-methyl-2,9-diphenyl-1,8,13,16-tetraoxa-dispiro[5.0.5.4]hexadecan-14-one

Guidance literature:: Multi-step reaction with 6 steps

1: LiBr / tetrahydrofuran / -78 °C

2: 98 percent / Ag₂O

4: 79 percent / H₂O, AcOH / tetrahydrofuran

5: 90 percent / NaBH₄ / ethanol / 0 °C

6: 92 percent / NaH, Bu₄NI

With sodium tetrahydroborate; water; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; lithium bromide; silver(l) oxide; In tetrahydrofuran; ethanol;