(2S,3S,4S,5S,6R)-2-(hydroxymethyl)-6-[(4-nitrophenyl)methoxy]tetrahydropyran-3,4,5-triol

Base Information

• Chemical Name: (2S,3S,4S,5S,6R)-2-(hydroxymethyl)-6-[(4-nitrophenyl)methoxy]tetrahydropyran-3,4,5-triol
• CAS No.: 211677-32-6
• Molecular Formula: C₁₃H₁₇NO₈
• Molecular Weight: 315.28

Synonyms:(2S,3S,4S,5S,6R)-2-(hydroxymethyl)-6-[(4-nitrophenyl)methoxy]tetrahydropyran-3,4,5-triol

Chemical Property of (2S,3S,4S,5S,6R)-2-(hydroxymethyl)-6-[(4-nitrophenyl)methoxy]tetrahydropyran-3,4,5-triol

Chemical Property:

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Technology Process of (2S,3S,4S,5S,6R)-2-(hydroxymethyl)-6-[(4-nitrophenyl)methoxy]tetrahydropyran-3,4,5-triol

There total 4 articles about (2S,3S,4S,5S,6R)-2-(hydroxymethyl)-6-[(4-nitrophenyl)methoxy]tetrahydropyran-3,4,5-triol 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: 95.0%

p-nitrobenzyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (211677-37-1) → (2S,3S,4S,5S,6R)-2-(hydroxymethyl)-6-[(4-nitrophenyl)methoxy]tetrahydropyran-3,4,5-triol (211677-32-6,700368-52-1)

Guidance literature:

With sodium; In methanol; Ambient temperature;

DOI:10.1002/(SICI)1099-0690(199808)1998:8<1669::AID-EJOC1669>3.0.CO;2-Q

Reference yield:

4-nitrobenzyl chloride (619-73-8) → (2S,3S,4S,5S,6R)-2-(hydroxymethyl)-6-[(4-nitrophenyl)methoxy]tetrahydropyran-3,4,5-triol (211677-32-6,700368-52-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / 4 Angstroem molecular sieves, TMSOTf / acetonitrile; CH₂Cl₂ / 0 deg C, 45 min, RT, overnight

2: 95 percent / sodium / methanol / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium; In methanol; dichloromethane; acetonitrile;

DOI:10.1002/(SICI)1099-0690(199808)1998:8<1669::AID-EJOC1669>3.0.CO;2-Q

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate (121238-27-5) → (2S,3S,4S,5S,6R)-2-(hydroxymethyl)-6-[(4-nitrophenyl)methoxy]tetrahydropyran-3,4,5-triol (211677-32-6,700368-52-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / 4 Angstroem molecular sieves, TMSOTf / acetonitrile; CH₂Cl₂ / 0 deg C, 45 min, RT, overnight

2: 95 percent / sodium / methanol / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium; In methanol; dichloromethane; acetonitrile;

DOI:10.1002/(SICI)1099-0690(199808)1998:8<1669::AID-EJOC1669>3.0.CO;2-Q

upstream raw materials:

p-nitrobenzyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

4-nitrobenzyl chloride

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate

Downstream raw materials:

p-aminobenzyl α-D-mannopyranoside

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