[(2S,5R,6S)-5-Benzyloxy-2-benzyloxymethyl-6-methoxy-dihydro-pyran-(3E)-ylidene]-acetic acid methyl ester

Base Information

Chemical Name:[(2S,5R,6S)-5-Benzyloxy-2-benzyloxymethyl-6-methoxy-dihydro-pyran-(3E)-ylidene]-acetic acid methyl ester
CAS No.:138607-87-1
Molecular Formula:C₂₄H₂₈O₆
Molecular Weight:412.483
Hs Code.:

Synonyms:[(2S,5R,6S)-5-Benzyloxy-2-benzyloxymethyl-6-methoxy-dihydro-pyran-(3E)-ylidene]-acetic acid methyl ester

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Chemical Property of [(2S,5R,6S)-5-Benzyloxy-2-benzyloxymethyl-6-methoxy-dihydro-pyran-(3E)-ylidene]-acetic acid methyl ester

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Technology Process of [(2S,5R,6S)-5-Benzyloxy-2-benzyloxymethyl-6-methoxy-dihydro-pyran-(3E)-ylidene]-acetic acid methyl ester

There total 7 articles about [(2S,5R,6S)-5-Benzyloxy-2-benzyloxymethyl-6-methoxy-dihydro-pyran-(3E)-ylidene]-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: 96.0%

: 5927-18-4
trimethyl phosphonoacetate

: (2R,5R,6S)-5-Benzyloxy-2-benzyloxymethyl-6-methoxy-dihydro-pyran-3-one

: 138607-87-1
[(2S,5R,6S)-5-Benzyloxy-2-benzyloxymethyl-6-methoxy-dihydro-pyran-(3E)-ylidene]-acetic acid methyl ester

Guidance literature:: With potassium tert-butylate; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 ℃;
DOI:10.1021/jo00028a017

Reference yield:

: 100-39-0
benzyl bromide

: 138607-87-1
[(2S,5R,6S)-5-Benzyloxy-2-benzyloxymethyl-6-methoxy-dihydro-pyran-(3E)-ylidene]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1) NaOH / 1) THF, water, 30 min., 2) 12 h

2: pyridine / CH₂Cl₂ / 2 h

3: n-Bu₃SnH, AIBN / toluene / 1 h / 110 °C

4: 75 percent / NaBH₃CN, 3 Angstroem molecular sieves, HCl / tetrahydrofuran; diethyl ether / overnight

5: 1) (COCl)2, DMSO, 2) Et₃N

6: 96 percent / t-BuOK / tetrahydrofuran; dimethylformamide / 0 °C

With pyridine; hydrogenchloride; sodium hydroxide; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); 3 A molecular sieve; potassium tert-butylate; tri-n-butyl-tin hydride; sodium cyanoborohydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00028a017

Reference yield:

: 76375-66-1
methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

: 138607-87-1
[(2S,5R,6S)-5-Benzyloxy-2-benzyloxymethyl-6-methoxy-dihydro-pyran-(3E)-ylidene]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine / CH₂Cl₂ / 2 h

2: n-Bu₃SnH, AIBN / toluene / 1 h / 110 °C

3: 75 percent / NaBH₃CN, 3 Angstroem molecular sieves, HCl / tetrahydrofuran; diethyl ether / overnight

4: 1) (COCl)2, DMSO, 2) Et₃N

5: 96 percent / t-BuOK / tetrahydrofuran; dimethylformamide / 0 °C

With pyridine; hydrogenchloride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); 3 A molecular sieve; potassium tert-butylate; tri-n-butyl-tin hydride; sodium cyanoborohydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00028a017