(E)-(2R,3S)-3-Benzyloxymethyl-2-tert-butoxycarbonylamino-6-(tert-butyl-diphenyl-silanyloxy)-hex-4-enoic acid

Base Information

Chemical Name:(E)-(2R,3S)-3-Benzyloxymethyl-2-tert-butoxycarbonylamino-6-(tert-butyl-diphenyl-silanyloxy)-hex-4-enoic acid
CAS No.:208767-18-4
Molecular Formula:C₃₅H₄₅NO₆Si
Molecular Weight:603.831
Hs Code.:

Synonyms:(E)-(2R,3S)-3-Benzyloxymethyl-2-tert-butoxycarbonylamino-6-(tert-butyl-diphenyl-silanyloxy)-hex-4-enoic acid

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Chemical Property of (E)-(2R,3S)-3-Benzyloxymethyl-2-tert-butoxycarbonylamino-6-(tert-butyl-diphenyl-silanyloxy)-hex-4-enoic acid

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Technology Process of (E)-(2R,3S)-3-Benzyloxymethyl-2-tert-butoxycarbonylamino-6-(tert-butyl-diphenyl-silanyloxy)-hex-4-enoic acid

There total 1 articles about (E)-(2R,3S)-3-Benzyloxymethyl-2-tert-butoxycarbonylamino-6-(tert-butyl-diphenyl-silanyloxy)-hex-4-enoic acid 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: 89.0%

: 208767-17-3
tert-Butoxycarbonylamino-acetic acid (E)-(S)-4-benzyloxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-2-enyl ester

: 208767-18-4
(E)-(2R,3S)-3-Benzyloxymethyl-2-tert-butoxycarbonylamino-6-(tert-butyl-diphenyl-silanyloxy)-hex-4-enoic acid

Guidance literature:: With zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; -78 deg C to RT;
DOI:10.1016/S0040-4039(97)10855-3

Reference yield:

: 208767-18-4
(E)-(2R,3S)-3-Benzyloxymethyl-2-tert-butoxycarbonylamino-6-(tert-butyl-diphenyl-silanyloxy)-hex-4-enoic acid

: 202979-50-8
(3aR,7S,7aR)-7-Benzyloxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridine

Guidance literature:: Multi-step reaction with 5 steps

1: 1) N-methylmorpholine, ClCOOiBu, 2) N-hydroxythiopyridone Na salt, 3) tert-butylmercaptane / 1) THF, -20 deg C, 20 min, 2) THF, -20 deg C, 3) THF, RT, 45 min, irradiation

2: 88 percent / OsO₄, K₂CO₃, K₃, methanesulfonamide, (DHQD)2PHAL / toluene; H₂O; 2-methyl-propan-2-ol / Ambient temperature

3: 94 percent / 2,2-dimethoxypropane, p-TsOH / 24 h

4: 97 percent / Bu₄NF / tetrahydrofuran / 12 h

5: 1) Tf₂O, pyridine, 2) HCl, 3) NaHCO₃ / 1) CH₂Cl₂, 15 deg C, 1 h, 2) dioxane, 2 h, 3) dioxane, H₂O, 50 deg C

With 4-methyl-morpholine; pyridine; hydrogenchloride; osmium(VIII) oxide; methanesulfonamide; trifluoromethylsulfonic anhydride; N-hydroxythiopyridone Na salt; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; 2-methylpropan-2-thiol; 1,4-bis(9-O-dihydroquinidine)phthalazine; 2,2-dimethoxy-propane; potassium hexacyanoferrate(III); isobutyl chloroformate; In tetrahydrofuran; water; toluene; tert-butyl alcohol;
DOI:10.1002/(sici)1099-0690(199806)1998:6<1155::aid-ejoc1155>3.0.co;2-g

Reference yield:

: 208767-18-4
(E)-(2R,3S)-3-Benzyloxymethyl-2-tert-butoxycarbonylamino-6-(tert-butyl-diphenyl-silanyloxy)-hex-4-enoic acid

: 202979-49-5
[(S)-3-Benzyloxy-2-((4R,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-propyl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1) N-methylmorpholine, ClCOOiBu, 2) N-hydroxythiopyridone Na salt, 3) tert-butylmercaptane / 1) THF, -20 deg C, 20 min, 2) THF, -20 deg C, 3) THF, RT, 45 min, irradiation

2: 88 percent / OsO₄, K₂CO₃, K₃, methanesulfonamide, (DHQD)2PHAL / toluene; H₂O; 2-methyl-propan-2-ol / Ambient temperature

3: 94 percent / 2,2-dimethoxypropane, p-TsOH / 24 h

4: 97 percent / Bu₄NF / tetrahydrofuran / 12 h

With 4-methyl-morpholine; osmium(VIII) oxide; methanesulfonamide; N-hydroxythiopyridone Na salt; tetrabutyl ammonium fluoride; potassium carbonate; toluene-4-sulfonic acid; 2-methylpropan-2-thiol; 1,4-bis(9-O-dihydroquinidine)phthalazine; 2,2-dimethoxy-propane; potassium hexacyanoferrate(III); isobutyl chloroformate; In tetrahydrofuran; water; toluene; tert-butyl alcohol;
DOI:10.1002/(sici)1099-0690(199806)1998:6<1155::aid-ejoc1155>3.0.co;2-g