(2S,6S,7S,9S,15R)-15-{(2S,5R,6R,8S)-8-[(S)-2-(Benzothiazole-2-sulfonyl)-1-methyl-ethyl]-5-benzyloxy-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)-8-[(S)-2-(Benzothiazole-2-sulfonyl)-1-methyl-ethyl]-5-benzyloxy-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.: 220690-91-5
• Molecular Formula: C₅₃H₅₉NO₁₀S₂
• Molecular Weight: 934.184
• Mol file: 220690-91-5.mol

Synonyms:(2S,6S,7S,9S,15R)-15-{(2S,5R,6R,8S)-8-[(S)-2-(Benzothiazole-2-sulfonyl)-1-methyl-ethyl]-5-benzyloxy-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

Chemical Property of (2S,6S,7S,9S,15R)-15-{(2S,5R,6R,8S)-8-[(S)-2-(Benzothiazole-2-sulfonyl)-1-methyl-ethyl]-5-benzyloxy-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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,6S,7S,9S,15R)-15-{(2S,5R,6R,8S)-8-[(S)-2-(Benzothiazole-2-sulfonyl)-1-methyl-ethyl]-5-benzyloxy-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 18 articles about (2S,6S,7S,9S,15R)-15-{(2S,5R,6R,8S)-8-[(S)-2-(Benzothiazole-2-sulfonyl)-1-methyl-ethyl]-5-benzyloxy-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: 78.0%

(2S,6S,7S,9S,15R)-15-{(2S,5R,6R,8S)-8-[(S)-2-(Benzothiazol-2-ylsulfanyl)-1-methyl-ethyl]-5-benzyloxy-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 (220691-75-8) → (2S,6S,7S,9S,15R)-15-{(2S,5R,6R,8S)-8-[(S)-2-(Benzothiazole-2-sulfonyl)-1-methyl-ethyl]-5-benzyloxy-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 (220690-91-5)

Guidance literature:

With ammonium molybdate tetrahydrate; dihydrogen peroxide; In ethanol;

Reference yield:

(6S,6'S)-6,6'-Diphenyl-5,6,5',6'-tetrahydro-4H,4'H-[2,2']bipyranyl (154859-09-3) → (2S,6S,7S,9S,15R)-15-{(2S,5R,6R,8S)-8-[(S)-2-(Benzothiazole-2-sulfonyl)-1-methyl-ethyl]-5-benzyloxy-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 (220690-91-5)

Guidance literature:

Multi-step reaction with 15 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

13: 95 percent / TBAF / tetrahydrofuran

14: 76 percent / Ph₃P, DEAD / tetrahydrofuran / -5 - 20 °C

15: 78 percent / Mo₇O₂₄(NH₄)6*4H₂O, H₂O₂ / aq. ethanol

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); ammonium molybdate tetrahydrate; dimethylsulfide borane complex; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; triphenylphosphine hydrobromide; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; triphenylphosphine; lithium chloride; potassium hexacyanoferrate(III); lithium diisopropyl amide; diethylazodicarboxylate; 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 → (2S,6S,7S,9S,15R)-15-{(2S,5R,6R,8S)-8-[(S)-2-(Benzothiazole-2-sulfonyl)-1-methyl-ethyl]-5-benzyloxy-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 (220690-91-5)

Guidance literature:

Multi-step reaction with 9 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

7: 95 percent / TBAF / tetrahydrofuran

8: 76 percent / Ph₃P, DEAD / tetrahydrofuran / -5 - 20 °C

9: 78 percent / Mo₇O₂₄(NH₄)6*4H₂O, H₂O₂ / aq. ethanol

With sodium tetrahydroborate; ammonium molybdate tetrahydrate; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; triphenylphosphine; lithium bromide; silver(l) oxide; diethylazodicarboxylate; In tetrahydrofuran; ethanol;

upstream raw materials:

(2S,6S,7S,9S,15R)-15-{(2S,5R,6R,8S)-8-[(S)-2-(Benzothiazol-2-ylsulfanyl)-1-methyl-ethyl]-5-benzyloxy-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

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

tert-Butyl-[(R)-2-((2S,4S)-4-methoxy-4-methyl-3,4-dihydro-2H-pyran-2-yl)-propoxy]-diphenyl-silane

(2S,6R,7S,9S)-2,9-Diphenyl-1,8,13,16-tetraoxa-dispiro[5.0.5.4]hexadecan-14-one