(S)-1-((2R,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-{(2R,6R)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-methylene-tetrahydro-pyran-2-ylmethyl}-tetrahydro-pyran-2-yl)-ethane-1,2-diol

Base Information

Chemical Name:(S)-1-((2R,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-{(2R,6R)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-methylene-tetrahydro-pyran-2-ylmethyl}-tetrahydro-pyran-2-yl)-ethane-1,2-diol
CAS No.:193416-65-8
Molecular Formula:C₄₀H₅₄O₇Si
Molecular Weight:674.95
Hs Code.:

(S)-1-((2R,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-{(2R,6R)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-methylene-tetrahydro-pyran-2-ylmethyl}-tetrahydro-pyran-2-yl)-ethane-1,2-diol

Synonyms:(S)-1-((2R,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-{(2R,6R)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-methylene-tetrahydro-pyran-2-ylmethyl}-tetrahydro-pyran-2-yl)-ethane-1,2-diol

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Chemical Property of (S)-1-((2R,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-{(2R,6R)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-methylene-tetrahydro-pyran-2-ylmethyl}-tetrahydro-pyran-2-yl)-ethane-1,2-diol

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Technology Process of (S)-1-((2R,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-{(2R,6R)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-methylene-tetrahydro-pyran-2-ylmethyl}-tetrahydro-pyran-2-yl)-ethane-1,2-diol

There total 13 articles about (S)-1-((2R,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-{(2R,6R)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-methylene-tetrahydro-pyran-2-ylmethyl}-tetrahydro-pyran-2-yl)-ethane-1,2-diol 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: 97.0%

: 193416-52-3
tert-Butyl-((2R,4R,6R)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-{(2R,6R)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-methylene-tetrahydro-pyran-2-ylmethyl}-tetrahydro-pyran-4-yloxy)-diphenyl-silane

: 193416-65-8
(S)-1-((2R,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-{(2R,6R)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-methylene-tetrahydro-pyran-2-ylmethyl}-tetrahydro-pyran-2-yl)-ethane-1,2-diol

Guidance literature:: With toluene-4-sulfonic acid; In methanol;
DOI:10.1021/jo9708755

Reference yield:

: {2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-[2-(4-methoxy-benzyloxy)-ethyl]-3,6-dihydro-2H-pyran-4-yloxy}-triethyl-silane

: 193416-65-8
(S)-1-((2R,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-{(2R,6R)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-methylene-tetrahydro-pyran-2-ylmethyl}-tetrahydro-pyran-2-yl)-ethane-1,2-diol

Guidance literature:: Multi-step reaction with 11 steps

1: TBAF, TsOH / tetrahydrofuran

2: 97 percent / K(s-Bu₃BH) / tetrahydrofuran

3: 93 percent / Et₃N

4: 97 percent / DDQ / CH₂Cl₂

5: 80 percent

6: CrCl₂/NiCl₂ / tetrahydrofuran

7: 1.) PNBA, Ph₃P, DEAD, 2.) K₃CO₃ / 2.) MeOH

8: 96 percent / Et₃N / CH₂Cl₂

9: 94 percent / TBAF

10: 86 percent / Et₃N / acetonitrile / Heating

11: 97 percent / TsOH / methanol

With chromium dichloride; tetrabutyl ammonium fluoride; potassium tri-sec-butyl-borohydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; diethylazodicarboxylate; 4-nitro-benzoic acid; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1021/jo9708755

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 193416-65-8
(S)-1-((2R,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-{(2R,6R)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-methylene-tetrahydro-pyran-2-ylmethyl}-tetrahydro-pyran-2-yl)-ethane-1,2-diol

Guidance literature:: Multi-step reaction with 9 steps

1: 93 percent / Et₃N

2: 97 percent / DDQ / CH₂Cl₂

3: 80 percent

4: CrCl₂/NiCl₂ / tetrahydrofuran

5: 1.) PNBA, Ph₃P, DEAD, 2.) K₃CO₃ / 2.) MeOH

6: 96 percent / Et₃N / CH₂Cl₂

7: 94 percent / TBAF

8: 86 percent / Et₃N / acetonitrile / Heating

9: 97 percent / TsOH / methanol

With chromium dichloride; tetrabutyl ammonium fluoride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; diethylazodicarboxylate; 4-nitro-benzoic acid; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1021/jo9708755