((1S,2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-7-oxa-bicyclo[4.1.0]hept-2-yl)-acetic acid methyl ester

Base Information

Chemical Name:((1S,2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-7-oxa-bicyclo[4.1.0]hept-2-yl)-acetic acid methyl ester
CAS No.:215303-30-3
Molecular Formula:C₃₀H₃₂O₆
Molecular Weight:488.58
Hs Code.:

Synonyms:((1S,2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-7-oxa-bicyclo[4.1.0]hept-2-yl)-acetic acid methyl ester

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Chemical Property of ((1S,2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-7-oxa-bicyclo[4.1.0]hept-2-yl)-acetic acid methyl ester

Chemical Property:

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Technology Process of ((1S,2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-7-oxa-bicyclo[4.1.0]hept-2-yl)-acetic acid methyl ester

There total 10 articles about ((1S,2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-7-oxa-bicyclo[4.1.0]hept-2-yl)-acetic acid methyl ester 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:

: (2R,3R)-3-((E)-(1R,2S,3R)-1,2,3-Tris-benzyloxy-5-methoxycarbonyl-pent-4-enyl)-oxirane-2-carboxylic acid 2-thioxo-2H-pyridin-1-yl ester

: 215303-30-3
((1S,2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-7-oxa-bicyclo[4.1.0]hept-2-yl)-acetic acid methyl ester

Guidance literature:: With tri-n-butyl-tin hydride; In tetrahydrofuran; for 0.5h; Yield given; Irradiation;
DOI:10.1021/jo981211d

Reference yield:

: (2S,3R)-3-((E)-(1R,2S,3R)-1,2,3-Tris-benzyloxy-5-methoxycarbonyl-pent-4-enyl)-oxirane-2-carboxylic acid 2-thioxo-2H-pyridin-1-yl ester

: 215303-30-3
((1S,2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-7-oxa-bicyclo[4.1.0]hept-2-yl)-acetic acid methyl ester

Guidance literature:: With tri-n-butyl-tin hydride; In tetrahydrofuran; for 0.5h; Irradiation;
DOI:10.1021/jo981211d

Reference yield:

: 185987-56-8
2-(R)-3-(S)-4-(R)-tribenzyloxy-5-t-butyldimethylsilyloxy-pentanal

: 215303-30-3
((1S,2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-7-oxa-bicyclo[4.1.0]hept-2-yl)-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 86 percent / CH₂Cl₂ / 10 h

2: (DHQD)2-PHAL, K₃Fe(CN)6, K₂CO₃, CH₃SO₂NH₂, OsO₄, H₂O / 2-methyl-propan-2-ol / 36 h / 0 °C

3: 1.) sodium bis(trimethylsilyl)amide, 2.) p-nitrosulfonyl chloride, 3.) K₂CO₃ / 1) THF, -78 deg C, 20 min; 2) THF, -78 to -40 deg C, 50 min; 3) CH₃OH, 0 --> 25 deg C, 1.5 h

4: 88 percent / HF / acetonitrile / 2.5 h / -20 - -10 °C

5: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1) CH₂Cl₂, -78 deg C, 40 min; 2) CH₂Cl₂, -78 to -30 deg C, 15 min; 3) CH₂Cl₂, -30 deg C --> rt, 6 h

6: 85 percent / aq. LiOH / tetrahydrofuran / 1) 10 deg C --> rt, 2 h; 2) rt, 2 h

7: 1.) isobutyl chloroformate, N-methylmorpholine / 1) THF, -23 deg C, 5 min; 2) THF, -23 deg C, 3 h

8: n-Bu₃SnH / tetrahydrofuran / 0.5 h / Irradiation

With 4-methyl-morpholine; lithium hydroxide; osmium(VIII) oxide; oxalyl dichloride; methanesulfonamide; p-nitrosulfonyl chloride; hydrogen fluoride; water; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; potassium carbonate; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; potassium hexacyanoferrate(III); isobutyl chloroformate; In tetrahydrofuran; dichloromethane; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo981211d