3-((2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-4-carboxymethyl-6-methoxy-tetrahydro-pyran-2-yl)-propionic acid ethyl ester

Base Information

Chemical Name:3-((2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-4-carboxymethyl-6-methoxy-tetrahydro-pyran-2-yl)-propionic acid ethyl ester
CAS No.:740840-55-5
Molecular Formula:C₂₇H₃₄O₈
Molecular Weight:486.562
Hs Code.:

Synonyms:3-((2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-4-carboxymethyl-6-methoxy-tetrahydro-pyran-2-yl)-propionic acid ethyl ester

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Chemical Property of 3-((2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-4-carboxymethyl-6-methoxy-tetrahydro-pyran-2-yl)-propionic acid ethyl ester

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Technology Process of 3-((2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-4-carboxymethyl-6-methoxy-tetrahydro-pyran-2-yl)-propionic acid ethyl ester

There total 4 articles about 3-((2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-4-carboxymethyl-6-methoxy-tetrahydro-pyran-2-yl)-propionic acid ethyl 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:

: 365418-34-4
methyl 2-O-benzyl-4,6-di-O-benzylidene-3-allyl-3-deoxy-α-D-glucopyranoside

: 740840-55-5
3-((2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-4-carboxymethyl-6-methoxy-tetrahydro-pyran-2-yl)-propionic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 62 percent / LiAlH₄; AlCl₃ / diethyl ether; CH₂Cl₂ / 2 h / 23 °C

2: 810 mg / CH₂Cl₂ / 6 h / 23 °C

3: 98 percent / NaBH₄; CuCl₂ / methanol / 0 - 20 °C

4: OsO₄; aq. NaIO₄ / tetrahydrofuran / 12 h / 20 °C

5: 520 mg / 2-methyl-2-butene; aq. NaClO₂; K₂HPO₄ / 2-methyl-propan-2-ol / 12 h / 20 °C

With sodium chlorite; sodium tetrahydroborate; sodium periodate; dipotassium hydrogenphosphate; osmium(VIII) oxide; lithium aluminium tetrahydride; aluminium trichloride; 2-methyl-but-2-ene; copper dichloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; tert-butyl alcohol; 2: Wittig reaction;
DOI:10.1002/anie.200353478

Reference yield:

: 740840-52-2
methyl (3R)-3-allyl-2,4-di-O-benzyl-3-deoxy-β-D-glucopyranoside

: 740840-55-5
3-((2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-4-carboxymethyl-6-methoxy-tetrahydro-pyran-2-yl)-propionic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 810 mg / CH₂Cl₂ / 6 h / 23 °C

2: 98 percent / NaBH₄; CuCl₂ / methanol / 0 - 20 °C

3: OsO₄; aq. NaIO₄ / tetrahydrofuran / 12 h / 20 °C

4: 520 mg / 2-methyl-2-butene; aq. NaClO₂; K₂HPO₄ / 2-methyl-propan-2-ol / 12 h / 20 °C

With sodium chlorite; sodium tetrahydroborate; sodium periodate; dipotassium hydrogenphosphate; osmium(VIII) oxide; 2-methyl-but-2-ene; copper dichloride; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol; 1: Wittig reaction;
DOI:10.1002/anie.200353478

Reference yield:

: 740840-53-3
(E)-3-((2R,3S,4S,5R,6S)-4-Allyl-3,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-acrylic acid ethyl ester

: 740840-55-5
3-((2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-4-carboxymethyl-6-methoxy-tetrahydro-pyran-2-yl)-propionic acid ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 98 percent / NaBH₄; CuCl₂ / methanol / 0 - 20 °C

2: OsO₄; aq. NaIO₄ / tetrahydrofuran / 12 h / 20 °C

3: 520 mg / 2-methyl-2-butene; aq. NaClO₂; K₂HPO₄ / 2-methyl-propan-2-ol / 12 h / 20 °C

With sodium chlorite; sodium tetrahydroborate; sodium periodate; dipotassium hydrogenphosphate; osmium(VIII) oxide; 2-methyl-but-2-ene; copper dichloride; In tetrahydrofuran; methanol; tert-butyl alcohol;
DOI:10.1002/anie.200353478